Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and fungicides

ABSTRACT

Provided herein are synergistic herbicidal compositions containing (a) a compound of formula (I): 
                         
or an agriculturally acceptable salt or ester thereof and (b) fungicides, including but not limited to, azoxystrobin, carbendazim, difenoconazole, flutolanil, hexaconazole, iprobenfos, isoprothiolane, isotianil, kasugamycin, mancozeb, myclobutanil, phthalide, probenazole, propiconazole, pyroquilon, tebuconazole, thifluzamide, tricyclazole, trifloxystrobin, validamycin, and a compound of formula (II)
 
     
       
         
         
             
             
         
       
     
     The compositions and methods provided herein control undesirable vegetation, e.g., in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, plantation crops, vegetables, industrial vegetation management (IVM) and rights of way (ROW).

FIELD

Provided herein are compositions comprising (a)4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylicacid or an agriculturally acceptable ester or salt thereof and (b)fungicides. Provided herein are also methods of controlling undesirablevegetation comprising applying (a)4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylicacid or an agriculturally acceptable ester or salt thereof and (b)fungicides.

BACKGROUND

The protection of crops from weeds and other vegetation which inhibitcrop growth is a constantly recurring problem in agriculture. To helpcombat this problem, researchers in the field of synthetic chemistryhave produced an extensive variety of chemicals and chemicalformulations effective in the control of such unwanted growth. Chemicalherbicides of many types have been disclosed in the literature and alarge number are in commercial use. However, there remains a need forcompositions and methods that are effective in controlling undesirablevegetation.

SUMMARY

A first embodiment including a herbicidal composition comprising aherbicidally effective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester thereof and (b)azoxystrobin, carbendazim, difenoconazole, flutolanil, hexaconazole,iprobenfos, isoprothiolane, isotianil, kasugamycin, mancozeb,myclobutanil, phthalide, probenazole, propiconazole, pyroquilon,tebuconazole, thifluzamide, tricyclazole, trifloxystrobin, validamycin,and a compound of formula (II)

A second embodiment, including the composition according to the firstembodiment, wherein (a) is a C₁₋₄ alkyl or benzyl ester of compound (I).

A third embodiment, including the composition according to the firstembodiment, wherein (a) is a C₁₋₄ alkyl ester of compound (I).

A fourth embodiment including the composition according to the secondembodiment, wherein (a) is a benzyl ester of compound (I).

A fifth embodiment including the composition according to the firstembodimet, wherein (a) is the compound of formula (I), which is thecarboxylic acid.

A sixth embodiment including the compositions according to the firstthrough the fifth embodiments, further comprising at least one compoundselected from the group consisting of: a herbicide safener, carrier andadjuvant.

A seventh embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to azoxystrobin in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:500 to about 12:1.

An eighth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to carbendazim in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:375 to about 12:1.

A ninth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to difenoconazole in units of g to g, gae/ha to gae/ha, orgae/ha gai/ha is from about 1:250 to about 12:1.

A tenth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to flutolanil in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:500 to about 12:1.

An eleventh embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to hexaconazole in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:250 to about 60:1.

A twelfth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to iprobenfos in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:1,000 to about 3:1.

A thirteenth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to isoprothiolane in units of g to g, gae/ha to gae/ha, orgae/ha gai/ha is from about 3:11:500 to about 6:1.

A fourteenth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to isotianil in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:500 to about 30:1.

A fifteenth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to kasugamycin in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:250 to about 150:1.

A sixteenth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to mancozeb in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:2500 to about 12:1.

A seventeenth embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to myclobutanil in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:250 to about 12:1.

An eighteenth embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to phthalide in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:500 to about 15:1.

A nineteenth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to probenazole in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:2500 to about 6:1.

A twentieth embodiment including at least one composition according thefirst through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to propiconazole in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:250 to about 30:1.

A twenty-first embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to pyroquilon in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:1,500 to about 3:1.

A twenty-second embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to tebuconazole in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:250 to about 12:1.

A twenty-third embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to thifluzamide in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:375 to about 30:1.

A twenty-fourth embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to tricyclazole in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:375 to about 15:1.

A twenty-fifth embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to trifloxystrobin in units of g to g, gae/ha to gae/ha, orgae/ha gai/ha is from about 1:250 to about 30:1.

A twenty-sixth embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to validamycin in units of g to g, gae/ha to gae/ha, or gae/hagai/ha is from about 1:25 to about 3,000:1.

A twenty-seventh embodiment including at least one composition accordingthe first through the sixth embodiments the wherein the ratios of thecompound of formula (I) or agriculturally acceptable salt or esterthereof to a compound of formula (II) in units of g to g, gae/ha togae/ha, or gae/ha gai/ha is from about 1:375 to about 150:1.

A twenty-eighth embodiment includes methods for controlling undesirablevegetation which comprises contacting the vegetation or the areaadjacent to the vegetation with or applying to the soil or water toprevent the emergence or growth of vegetation the composition of any ofthe composition according to the first through the twenty-seventhembodiments.

A twenty-ninth embodiment includes methods of controlling undesirablevegetation which comprises contacting the vegetation or the areaadjacent to the vegetation with or applying to the soil or water toprevent the emergence or growth of vegetation a herbicidally effectiveamount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester thereof and (b)azoxystrobin, carbendazim, difenoconazole, flutolanil, hexaconazole,iprobenfos, isoprothiolane, isotianil, kasugamycin, mancozeb,myclobutanil, phthalide, probenazole, propiconazole, pyroquilon,tebuconazole, thifluzamide, tricyclazole, trifloxystrobin, validamycin,and a compound of formula (II)

A thirtieth embodiment includes methods according to the twenty-eighthand twenty-ninth embodiments for controlling undesired vegetation,wherein the undesirable vegetation is controlled in direct-seeded,water-seeded and transplanted rice, cereals, wheat, barley, oats, rye,sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugarbeet, soybean, cotton, pineapple, pastures, grasslands, rangelands,fallowland, turf, tree and vine orchards, plantation crops, vegetables,industrial vegetation management (IVM) and rights of way (ROW).

A thirty-first embodiment includes methods according to thetwenty-eighth and twenty-ninth embodiments, wherein the undesirablevegetation is immature.

A thirty-second embodiment includes methods according to thetwenty-eighth and twenty-ninth embodiments, wherein the compounds (a)and (b) are applied to water.

The thirty-third embodiment includes methods according to thethirty-second embodiment wherein the water is part of a flooded ricepaddy.

A thirty-fourth embodiment includes methods according to thetwenty-eighth and twenty-ninth embodiments wherein the compound (a) and(b) are applied pre-emergently and/or post emergently to the weed or thecrop.

A thirty-fifth embodiment includes methods according to thetwenty-eighth and twenty-ninth embodiments, wherein the undesirablevegetation is controlled in glyphosate-,5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-,glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-,pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-,aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetylCoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-,pyrimidinylthiobenzoate-, triazolopyrimidine-,sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) oracetohydroxy acid synthase (AHAS) inhibitor-, 4-hydroxyphenyl-pyruvatedioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-,carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO)inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-,microtubule inhibitor-, very long chain fatty acid inhibitor-, fattyacid and lipid biosynthesis inhibitor-, photosystem I inhibitor-,photosystem II inhibitor-, triazine-, or bromoxynil-tolerant crops.

A thirty-sixth embodiment includes methods according to the thirty-fifthembodiment, wherein the tolerant crop possesses multiple or stackedtraits conferring tolerance to multiple herbicides or multiple modes ofaction.

A thirty-seventh embodiment includes methods according to thetwenty-eighth and twenty-ninth embodiments, wherein the undesirablevegetation comprises a herbicide resistant or tolerant weed.

A thirty-eighth embodiment includes methods according to thethirty-seventh embodiment, wherein the resistant or tolerant weed is abiotype with resistance or tolerance to multiple herbicides, multiplechemical classes, multiple herbicide modes-of-action, or via multipleresistance mechanisms.

The thirty-ninth embodiment includes methods according to thetwenty-eighth and twenty-ninth embodiments, wherein the resistant ortolerant weed is a biotype resistant or tolerant to acetolactatesynthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors,photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors,synthetic auxins, auxin transport inhibitors, photosystem I inhibitors,5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,microtubule assembly inhibitors, fatty acid and lipid synthesisinhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoidbiosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors,phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors,4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosisinhibitors, cellulose biosynthesis inhibitors, herbicides with multiplemodes-of-action, quinclorac, arylaminopropionic acids, difenzoquat,endothall, or organoarsenicals.

Provided herein are herbicidal compositions comprising a herbicidallyeffective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester of thereof, and (b)fungicides. The compositions may also contain an agriculturallyacceptable adjuvant or carrier. Provided herein are also methods ofcontrolling undesirable vegetation comprising applying (a) a compound offormula (I) or an agriculturally acceptable ester or salt thereof and(b) fungicides.

DETAILED DESCRIPTION Definitions

As used herein, the compound of formula (I) has the following structure:

The compound of formula (I) can be identified by the name4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylicacid and has been described in U.S. Pat. No. 7,314,849 (B2), which isincorporated herein by reference in its entirety. Exemplary uses of thecompound of the formula (I) include controlling undesirable vegetation,including grass, broadleaf and sedge weeds, in multiple non-crop andcropping situations.

Fungicides are a class of pesticides used to control plant pathogens incrop and non-crop settings. Without being limited to any theory, thesepesticides kill diseases/plant pathogens via multiple, different modesof action. Exemplary uses of fungicides include their use to controlplant diseases and plant pathogens in cereal, legume, vegetable, fruit,row and perennial crops.

Exemplary fungicides include, but are not limited to, azoxystrobin,carbendazim, difenoconazole, flutolanil, hexaconazole, iprobenfos,isoprothiolane, isotianil, kasugamycin, mancozeb, myclobutanil,phthalide, probenazole, propiconazole, pyroquilon, tebuconazole,thifluzamide, tricyclazole, trifloxystrobin, validamycin, and a compoundof formula (II):

As used herein, azoxystrobin is methyl(E)-{2-[6(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}3-methoxyacrylate andpossesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of azoxystrobin include its use as a protectant,curative and eradicant fungicide for the control of many plant pathogensin crops, including Pyricularia and Rhizoctonia in rice. Azoxystrobincan be applied, e.g., as a post-emergence treatment to controlundesirable plant pathogens.

As used herein, carbendazim is methyl benzimidazol-2-ylcarbamate andpossesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of carbendazim include its use as a systemicfungicide with protective and curative action for the control ofSeptoria, Fusarium, Erysiphe and other diseases in cereals crops.Carbendazim can be applied, e.g., post-emergence to control undesirableplant pathogens.

As used herein difenoconazole is cis,trans-3-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3,dioxolan-2-yl]pheyl chlorophenyl ether and possesses the followingstructure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of difenoconazole include its use as a systemicfungicide with preventative and curative activity for the control ofplant diseases in many crops, including Rhizoctonia, Cercospora,Septoria and many other diseases in rice, cereals, oilseed rape, etc.Difenoconazole can be applied, e.g., as a post-emergence treatment tocontrol undesirable plant pathogens.

As used herein, flutolanil isα,α,α-trifluoro-3′-isopropoxy-o-toluanilide and possesses the followingstructure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of flutolanil include its use as a systemicfungicide for the control of Rhizoctonia in many crops, including rice,cereals, turf, etc. Flutolanil can be applied, e.g., as a post-emergencetreatment to control undesirable plant pathogens.

As used herein, hexaconazole is(RS)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol) andpossesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of hexaconazole include its use for the control ofAscomycetes and Basidiomycetes in vine, coffee, and other crops.Hexaconazole can be applied, e.g., as a post-emergence treatment tocontrol undesirable plant pathogens.

As used herein, iprobenfos is S-benzyl O,O-diisopropyl phosphorothioateand possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of Iprobenfos include its use as a systemicfungicide for the control of rice blast (Pyricularia), stem rot andsheath blight (Rhizoctonia) in rice. Iiprobenfos can be applied, e.g.,as a post-emergence treatment to control undesirable plant pathogens.

As used herein, isoprothiolane is diisopropyl1,3-dithiolan-2-ylidenemalonate and possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of isoprothiolane include its use as a systemicfungicide that inhibits penetration and elongation of infection hyphaefor the control of Pyricularia and other diseases in rice and othercrops. isoprothiolane can be applied, e.g., post-emergence treatment tocontrol undesirable plant pathogens.

As used herein isotianil is 3,4-dichloro-2′cyano-1,2-thiazole-5-carboxanilide and possesses the followingstructure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of isotianil include its use for the control ofrice blast (Pyricularia) in rice. isotianil can be applied, e.g.,post-emergence or rice nursery box drench treatment to controlundesirable plant pathogens.

As used herein, kasugamycin is11-1,3,4/2,5,6-1-deoxy-2,3,4,5,6,-pentahydroxycyclohexyl2-amino-2,3,4,6-tetradeoxy-4-(α-iminoglycino)-α-D-arabino-hexopyranosidehydrochloride hydrate and possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of kasugamycin include its use as a systemicfungicide and bactericide that inhibits hyphal growth of rice blast(Pyricularia) in rice. Kasugamycin can be applied, e.g., rice nurserydrench and post-emergence treatments to control undesirable plantpathogens.

As used herein, mancozeb is manganexe ethylenebis(dithiocarbamate)(polymeric) complex with zinc salt and possesses the followingstructure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of mancozeb include its use as a protectantfungicide for the control of many fungal diseases in many crops.Mancozeb in a fungal respiration inhibitor, and can be applied, e.g., asa post-emergence and seed treatment to control many undesirable plantpathogens.

As used herein, myclobutanil is2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile andpossesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of myclobutanil, a known ergosterol biosynthesisinhibitor with protective and curative properties, include its use forthe control of Ascomycetes, Fungi Imperfecti and Basidomycetes in manycrops. Myclobutanil can be applied, e.g., post-emergence and seedtreatment to control undesirable plant pathogens.

As used herein, phthalide is 4,5,6,7-tetrachlorophthalide and possessesthe following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of phthalide include its use for the control ofrice blast (Pyricularia oryzae) in rice. Phthalide can be applied, e.g.,drench and post-emergence to control rice blast in rice.

As used herein, probenazole, is 3-allyloxy-1,2-benz[d]isothiazole1,1-dioxide and possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of probenazole include its use for the control ofrice blast and leaf blight in transplanted rice. Probenazole can beapplied, e.g., post-emergence treatment to control undesirable plantpathogens in rice.

As used herein, propiconazole is142-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2 ylmethyl]1H-1,2,4-triazole and possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of propiconazole include its use for the control ofRhizoctonia and dirty panicle complex in rice, as well as many diseasesin cereal, turf and corn crops. Propiconazole can be applied, e.g.,post-emergence treatment to control undesirable plant pathogens in manycrops.

As used herein, pyroquilon is1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinolin-4-one and possesses thefollowing structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of pyroquilon, a known melanin biosynthesisinhibitor, include its use for the control of Pyricularia in rice.Pyroquilon can be applied, e.g., as a post-emergence and seed drenchtreatment to control undesirable plant pathogens in rice.

As used herein, tebuconazole is(RS)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-oland possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Tebuconazole acts by inhibition of ergosterol biosynthesis,providing protective, curative and eradicant activity. Exemplary uses oftebuconazole include its use for the control of many diseases acrossmany crops, including Puccinia, Fusarium, Erysiphe and other diseases.Tebuconazole can be applied, e.g., as a post-emergence treatment tocontrol undesirable plant pathogens.

As used herein, thifluzamide is2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5-carboxanilideand possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of thifluzamide include its use for the control ofBasidiomycetes diseases including Rhizoctonia in rice and cereal crops.Thifluzamide can be applied, e.g., post-emergence and seed treatment tocontrol undesirable plant pathogens.

As used herein, tricyclazole is5-methyl-1,2,4-triazolo[3,4-b][1,3]benzothiazole and possesses thefollowing structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of tricyclazole, a known melanin biosynthesisinhibitor, include its use for the control of rice blast (Pyriculariaoryzae) in seeded and transplanted rice. Tricyclazole can be applied,e.g., as a post-emergence, seed or soak treatment to control undesirableplant pathogens in rice.

As used herein, trifloxystrobin is methyl(E)-methoxyimino-{(E)-α-[1-(α,α,α-trifluoro-m-tolyl)ethylideneaminooxy]-o-tolyl}acetateand possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of trifloxystrobin include its use for the controlof rusts and powdery mildew in cereal, fruit and vegetable crops.Trifloxystrobin can be applied, e.g., as a post-emergence treatment tocontrol undesirable plant pathogens.

As used herein, validamycin is1L-(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-{[(1S,4S,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]aminol}cyclohexylβ-D-glucopyranoside and possesses the following structure:

Its fungicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of validamycin include its use for the control ofRhizoctonia solani in rice and many other crops. Validamycin can beapplied, e.g., post-mergence, soil drench or seed treatment to controlundesirable plant pathogens.

As used herein, a compound of formula (II) possesses the followingstructure:

Its fungicidal activity is exemplified in: International PatentPublication No. WO 03/035617, published May 1, 2003. Exemplary uses of acompound of formula (II) include its use for the control of rust andother diseases in cereal crops. A compound of formula (II) can beapplied, e.g., post-emergence treatment to control undesirable plantpathogens.

As used herein, fungicide means a compound, e.g., active ingredient thatkills, controls or otherwise adversely modifies the growth of plantdiseases/pathogens. As used herein, fungicide means a compound, e.g.,active ingredient that kills, controls or otherwise adversely modifiesthe growth of fungi.

As used herein, a fungicidal effective or controlling amount is anamount of active ingredient which causes an adversely modifying effectto the fungi to be controlled, e.g., causing deviations from naturaldevelopment, killing, effecting regulation, causing desiccation, causingretardation, and the like.

As used herein, controlling undesirable vegetation means preventing,reducing, killing, or otherwise adversely modifying the development ofplants and vegetation. Described herein are methods of controllingundesirable vegetation through the application of certain herbicide andfungicide combinations or compositions Methods of application include,but are not limited to applications to the vegetation or locus thereof,e.g., application to the area adjacent to the vegetation, as well aspre-emergence, post-emergence, foliar (broadcast, directed, banded,spot, mechanical, over-the-top, or rescue), and in-water applications(emerged and submerged vegetation, broadcast, spot, mechanical,water-injected, granular broadcast, granular spot, shaker bottle, orstream spray) via hand, backpack, machine, tractor, or aerial (airplaneand helicopter) application methods.

As used herein, plants and vegetation include, but are not limited to,germinant seeds, emerging seedlings, plants emerging from vegetativepropagules, immature vegetation, and established vegetation.

As used herein, agriculturally acceptable salts and esters refer tosalts and esters that exhibit herbicidal activity, or that are or can beconverted in plants, water, or soil to the referenced herbicide.Exemplary agriculturally acceptable esters are those that are or can byhydrolyzed, oxidized, metabolized, or otherwise converted, e.g., inplants, water, or soil, to the corresponding carboxylic acid which,depending on the pH, may be in the dissociated or undissociated form.

Exemplary salts include those derived from alkali or alkaline earthmetals and those derived from ammonia and amines Exemplary cationsinclude sodium, potassium, magnesium, and ammonium cations of theformula:R ¹ R ² R ³ R ⁴ N ⁺wherein R¹, R², R³ and R⁴ each, independently represents hydrogen orC₁-C₁₂ alkyl, C₃-C₁₂ alkenyl or C₃-C₁₂ alkynyl, each of which isoptionally substituted by one or more hydroxy, C₁-C₄ alkoxy, C₁-C₄alkylthio or phenyl groups, provided that R¹, R², R³ and R⁴ aresterically compatible. Additionally, any two of R¹, R², R³ and R⁴together may represent an aliphatic difunctional moiety containing oneto twelve carbon atoms and up to two oxygen or sulfur atoms. Salts canbe prepared by treatment with a metal hydroxide, such as sodiumhydroxide, with an amine, such as ammonia, trimethylamine,diethanolamine, 2-methylthiopropylamine, bisallylamine,2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine orwith a tetraalkylammonium hydroxide, such as tetramethylammoniumhydroxide or choline hydroxide.

Exemplary esters include those derived from C₁-C₁₂ alkyl, C₃-C₁₂alkenyl, C₃-C₁₂ alkynyl or C₂-C₁₀ aryl-substituted alkyl alcohols, suchas methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol,butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol,cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzylalcohols may be substituted with from 1-3 substituents independentlyselected from halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy. Esters can beprepared by coupling of the acids with the alcohol using any number ofsuitable activating agents such as those used for peptide couplings suchas dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); byreacting the acids with alkylating agents such as alkylhalides oralkylsulfonates in the presence of a base such as triethylamine orlithium carbonate; by reacting the corresponding acid chloride of anacid with an appropriate alcohol; by reacting the corresponding acidwith an appropriate alcohol in the presence of an acid catalyst or bytransesterification.

Compositions and Methods

Provided herein are herbicidal compositions comprising a herbicidallyeffective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester of thereof, and (b)fungicides, including but not limited to, azoxystrobin, carbendazim,difenoconazole, flutolanil, hexaconazole, iprobenfos, isoprothiolane,isotianil, kasugamycin, mancozeb, myclobutanil, phthalide, probenazole,propiconazole, pyroquilon, tebuconazole, thifluzamide, tricyclazole,trifloxystrobin, validamycin, and a compound of formula (II).

Provided herein are also methods of controlling undesirable vegetationcomprising contacting the vegetation or locus thereof, i.e., the areaadjacent to the vegetation with or applying to the soil or water toprevent the emergence or growth of vegetation a herbicidally effectiveamount of the compound of formula (I) or agriculturally acceptable saltor ester thereof and (b) fungicides, including but not limited to,azoxystrobin, carbendazim, difenoconazole, flutolanil, hexaconazole,iprobenfos, isoprothiolane, isotianil, kasugamycin, mancozeb,myclobutanil, phthalide, probenazole, propiconazole, pyroquilon,tebuconazole, thifluzamide, tricyclazole, trifloxystrobin, validamycin,and a compound of formula (II). In certain embodiments, the methodsemploy the compositions described herein.

Furthermore, in some embodiments, the combination of compound (I) oragriculturally acceptable salt or ester thereof and azoxystrobin,carbendazim, difenoconazole, flutolanil, hexaconazole, iprobenfos,isoprothiolane, isotianil, kasugamycin, mancozeb, myclobutanil,phthalide, probenazole, propiconazole, pyroquilon, tebuconazole,thifluzamide, tricyclazole, trifloxystrobin, validamycin, and a compoundof formula (II) exhibits synergism, e.g., the herbicidal activity ismore effective in combination than when compound of formula (I) isapplied individually. Synergism has been defined as “an interaction oftwo or more factors such that the effect when combined is greater thanthe predicted effect based on the response of each factor appliedseparately.” Senseman, S., ed. Herbicide Handbook. 9^(th) ed. Lawrence:Weed Science Society of America, 2007. In certain embodiments, thecompositions exhibit synergy as determined by the Colby's equation.Colby, S. R. 1967. Calculation of the synergistic and antagonisticresponse of herbicide combinations. Weeds 15:20-22.

In certain embodiments of the compositions and methods described herein,the compound of formula (I), i.e., the carboxylic acid, is employed. Incertain embodiments, a carboxylate salt of the compound of formula (I)is employed. In certain embodiments, an aralkyl or alkyl ester isemployed. In certain embodiments, a benzyl, substituted benzyl, or C₁₋₄alkyl, e.g., n-butyl ester is employed. In certain embodiments, thebenzyl ester is employed.

In some embodiments, the compound of formula (I) or salt or esterthereof and azoxystrobin, carbendazim, difenoconazole, flutolanil,hexaconazole, iprobenfos, isoprothiolane, isotianil, kasugamycin,mancozeb, myclobutanil, phthalide, probenazole, propiconazole,pyroquilon, tebuconazole, thifluzamide, tricyclazole, trifloxystrobin,validamycin, and a compound of formula (II) are formulated in onecomposition, tank mixed, applied simultaneously, or appliedsequentially.

Herbicidal activity is exhibited by the compounds when they are applieddirectly to the plant or to the area adjacent to the plant at any stageof growth. The effect observed depends upon the plant species to becontrolled, the stage of growth of the plant, the application parametersof dilution and spray drop size, the particle size of solid components,the environmental conditions at the time of use, the specific compoundemployed, the specific adjuvants and carriers employed, the soil type,and the like, as well as the amount of chemical applied. These and otherfactors can be adjusted to promote non-selective or selective herbicidalaction. In some embodiments, the compositions described herein areapplied as a post-emergence application, pre-emergence application, orin-water application to flooded paddy rice or water bodies (e.g., ponds,lakes and streams), to relatively immature undesirable vegetation toachieve the maximum control of weeds.

In some embodiments, the compositions and methods provided herein areutilized to control weeds in crops, including but not limited todirect-seeded, water-seeded and transplanted rice, cereals, wheat,barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseedrape, canola, sugar beet, soybean, cotton, pineapple, pastures,grasslands, rangelands, fallowland, turf, tree and vine orchards,plantation crops, vegetables, industrial vegetation management (IVM) andrights of way (ROW).

In certain embodiments, the compositions and methods provided herein areutilized to control weeds in rice. In certain embodiments, the rice isdirect-seeded, water-seeded, or transplanted rice.

The compositions and methods described herein may be used to controlundesirable vegetation in glyphosate-tolerant-,5-enolpyruvylshikimate-3-phosphate (EP SP) synthase inhibitor-tolerant-,glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-,dicamba-tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-,auxin-tolerant-, auxin transport inhibitor-tolerant-,aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-,phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase)inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-,pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-,sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS)or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerant-,phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesisinhibitor-tolerant-, protoporphyrinogen oxidase (PPO)inhibitor-tolerant-, cellulose biosynthesis inhibitor-tolerant-, mitosisinhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chainfatty acid inhibitor-tolerant-, fatty acid and lipid biosynthesisinhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem IIinhibitor-tolerant-, triazine-tolerant- and bromoxynil-tolerant-crops(such as, but not limited to, soybean, cotton, canola/oilseed rape,rice, cereals, corn, sorghum, sunflower, sugar beet, sugarcane, turf,etc), for example, in conjunction with glyphosate, EPSP synthaseinhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxyauxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors,aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCaseinhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHASinhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoidbiosynthesis inhibitors, PPO inhibitors, cellulose biosynthesisinhibitors, mitosis inhibitors, microtubule inhibitors, very long chainfatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors,photosystem I inhibitors, photosystem II inhibitors, triazines, andbromoxynil. The compositions and methods may be used in controllingundesirable vegetation in crops possessing multiple or stacked traitsconferring tolerance to multiple chemistries and/or inhibitors ofmultiple modes of action. In some embodiments, the compound of formula(I) or salt or ester thereof and complementary herbicide or salt orester thereof are used in combination with herbicides that are selectivefor the crop being treated and which complement the spectrum of weedscontrolled by these compounds at the application rate employed. In someembodiments, the compositions described herein and other complementaryherbicides are applied at the same time, either as a combinationformulation or as a tank mix, or sequentially.

The compositions and methods may be used in controlling undesirablevegetation in crops possessing agronomic stress tolerance (including butnot limited to drought, cold, heat, salt, water, nutrient, fertility,pH), pest tolerance (including but not limited to insects, fungi andpathogens) and crop improvement traits (including but not limited toyield; protein, carbohydrate, or oil content; protein, carbohydrate, oroil composition; plant stature and plant architecture).

The compositions and methods provided herein are utilized to controlundesirable vegetation. Undesirable vegetation includes, but is notlimited to, undesirable vegetation that occurs in rice, cereals, wheat,barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseedrape, canola, sugar beet, soybean, cotton, pineapple, pastures,grasslands, rangelands, fallowland, turf, tree and vine orchards,aquatics, plantation crops, vegetables, industrial vegetation management(IVM) and rights of way (ROW).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in rice. In certain embodiments, the undesirablevegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloaplatyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloaspecies (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass,ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV),Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides(Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola(Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon(Stapf) Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya(Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb.(saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinesesprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (beardedsprangletop, LEFFA), Leptochloa panicoides (Presl) Hitchc. (Amazonsprangletop, LEFPA), Oryza species (red and weedy rice, ORYSS), Panicumdichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatumPoir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W. D.Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus difformisL. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU),Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (riceflatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO),Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globefringerush, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectusjuncoides Roxb. (Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.)Palla or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA),Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU), Aeschynomenespecies, (jointvetch, AESSS), Alternanthera phdoxeroides (Mart.) Griseb.(alligatorweed, ALRPH), Alisma plantago-aquatica L. (commonwaterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths,AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelinabenghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk.(American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl(ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleafmudplantain, HETRE), Ipomoea species (morningglories, IPOSS), Ipomoeahederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L.)Pennell (low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigialinifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigiaoctovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC),Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoriavaginalis (Berm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannianudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L.,(Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb,POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotalaindica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species,(arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hempsesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in cereals. In certain embodiments, theundesirable vegetation is Alopecurus myosuroides Huds. (blackgrass,ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L.(wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Loliummultiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz.(littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN),Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU),Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthusretroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS),Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.)Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw,GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureumL. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile,MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT),Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wildbuckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapisspecies (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellariamedia (L.) Vill. (common chickweed, STEME), Veronica persica Poir.(Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR),or Viola tricolor L. (wild violet, VIOTR).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in range and pasture, fallowland, IVM and ROW. Incertain embodiments, the undesirable vegetation is Ambrosiaartemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sicklepod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed,CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulusarvensis L. (field bindweed, CONAR), Euphorbia esula L. (leafy spurge,EPHES), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Plantagolanceolata L. (buckhorn plantain, PLALA), Rumex obtusifolius L.(broadleaf dock, RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapisarvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennialsowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacumofficinale G. H. Weber ex Wiggers (dandelion, TAROF), Trifolium repensL. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation found in row crops, tree and vine crops, andperennial crops. In certain embodiments, the undesirable vegetation isAlopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wildoat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf)R. D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. exA. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R. D.(beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloaplatyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southernsandbar, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass,DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloacrus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum(L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn. (goosegrass,ELEIN), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicumdichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L.(wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail,SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghumhalepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moenchssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellownutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilontheophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds andamaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL),Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L.(giant ragweed, AMBTR), Anoda cristata (L.) Schlecht. (spurred anoda,ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L.(hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata(Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed, BOILF),Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium albumL. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canadathistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE),Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot,DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbiahirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI),Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensisL. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeroncanadensis L. or Conyza canadensis (L.) Cronq. (Canadian fleabane,ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL),Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia(L.) Griseb. (smallflower morningglory, IAQTA), Ipomoea hederacea (L.)Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (whitemorningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce,LACSE), Portulaca oleracea L. (common purslane, POROL), Richardiaspecies (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L.(prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR),Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridaxprocumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (commoncocklebur, XANST).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in turf In certain embodiments, the undesirablevegetation is Bellis perennis L. (English daisy, BELPE), Cyperusesculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodiavirginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge,EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellataL. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamiumamplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan(doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L.(broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhorn/narrowleafplantain, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumexobtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew.(Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed,STEME), Taraxacum officinale G. H. Weber ex Wiggers (dandelion, TAROF),Trifolium repens L. (white clover, TRFRE), or Viola species (wildviolet, VIOSS).

In some embodiments, the compositions and methods provided herein areutilized to control undesirable vegetation consisting of grass,broadleaf and sedge weeds. In certain embodiments, the compositions andmethods provided herein are utilized to control undesirable grass,broadleaf and sedge vegetation including but not limited toBrachiaria/Uroichloa, Cyperus, Digitaria, Echinochloa, Fimbristylis,Ipomoea, Leptochloa, and Schoenoplectus.

In some embodiments, the combination of compound (I) or agriculturallyacceptable ester or salt thereof and fungicides are used to control,including but not limited to, broadleaf signalgrass (Brachiariaplatyphylla (Groseb.) Nash), yellow nutsedge (Cyperus esculentus L.),rice flatsedge (Cyperus iria L.), purple nutsedge (Cyperus rotundus),large crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrus-galli), jungle rice (Echinochloa colona), watergrass (Echinochloaoryzoides), globe fringerush (Fimbristylis miliacea (L.) Vahl), ivyleafmorningglory (Ipomoea hederacea), Chinese sprangletop (Leptochloachinensis) and Japanese bulrush (Schoenoplectus juncoides).

The compounds of formula I or agriculturally acceptable salt or esterthereof may be used to control herbicide resistant or tolerant weeds.The methods employing the combination of a compound of formula I oragriculturally acceptable salt or ester thereof and the compositionsdescribed herein may also be employed to control herbicide resistant ortolerant weeds. Exemplary resistant or tolerant weeds include, but arenot limited to, biotypes resistant or tolerant to acetolactate synthase(ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g.,imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem IIinhibitors (e.g., phenylcarbamates, pyridazinones, triazines,triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles,phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g.,aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines),synthetic auxins (e.g., benzoic acids, phenoxycarboxylic acids, pyridinecarboxylic acids, quinoline carboxylic acids), auxin transportinhibitors (e.g., phthalamates, semicarbazones), photosystem Iinhibitors (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate(EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetaseinhibitors (e.g., glufosinate, bialafos), microtubule assemblyinhibitors (e.g., benzamides, benzoic acids, dinitroanilines,phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates),very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides,chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipidsynthesis inhibitors (e.g., phosphorodithioates, thiocarbamates,benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO)inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles,oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles,triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone,amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g.,amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones,pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors(e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulosebiosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac,triazolocarboxamides), herbicides with multiple modes-of-action such asquinclorac, and unclassified herbicides such as arylaminopropionicacids, difenzoquat, endothall, and organoarsenicals. Exemplary resistantor tolerant weeds include, but are not limited to, biotypes withresistance or tolerance to multiple herbicides, biotypes with resistanceor tolerance to multiple chemical classes, and biotypes with resistanceor tolerance to multiple herbicide modes-of-action, and biotypes withmultiple resistance or tolerance mechanisms (e.g., target siteresistance or metabolic resistance).

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with azoxystrobin. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to azoxystrobin is within the range of from about 1:500 toabout 12:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to azoxystrobin is within the rangeof from about 1:57 to about 1:2. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 27 grams active ingredient per hectare (gai/ha) to about 1300gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 66 grams active ingredient per hectare(gai/ha) to about 300 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andazoxystrobin, e.g., sequentially or simultaneously. In some embodiments,azoxystrobin is applied at a rate from about 25 gai/ha to about 1000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, azoxystrobin is applied at a rate from about 62 gai/ha toabout 250 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 4 g acid equivalent per hectare(gae/ha) to about 32 gae/ha. In certain embodiments, the methods utilizethe compound of formula (I), or its benzyl ester and azoxystrobin. Inone embodiment, the methods utilize the compound of formula (I) andazoxystrobin, wherein the compound of formula (I) is applied at a rateof from about 3 g acid equivalent per hectare (gae/ha) to about 200gae/ha, and azoxystrobin is applied at a rate of about 30 gai/ha toabout 900 gai/ha. In one embodiment, the methods utilize the benzylester of the compound of formula (I) and azoxystrobin, wherein thebenzyl ester of the compound of formula (I) is applied at a rate of fromabout 4.4 g acid equivalent per hectare (gae/ha) to about 32 gae/ha, andazoxystrobinis applied at a rate of about 62 gai/ha to about 250 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with carbendazim. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to carbendazim is within the range of from about 1:375 toabout 12:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to carbendazim is within the rangeof from about 1:31 to about 1:4. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 27 grams active ingredient per hectare (gai/ha) to about1,050 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 133 grams active ingredient per hectare(gai/ha) to about 282 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andcarbendazim, e.g., sequentially or simultaneously. In some embodiments,carbendazimis applied at a rate from about 25 gai/ha to about 750 gai/haand the compound of formula (I) of salt or ester thereof is applied at arate from about 2 gae/ha to about 300 gae/ha. In some embodiments,carbendazim is applied at a rate from about 50 gai/ha to about 600gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 3 g acid equivalent per hectare (gae/ha) toabout 200 gae/ha. In certain embodiments, the methods utilize thecompound of formula (I), or its benzyl ester and carbendazim. In oneembodiment, the methods utilize the compound of formula (I) andcarbendazim, wherein the compound of formula (I) is applied at a rate offrom about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,and carbendazim is applied at a rate of about 50 gai/ha to about 600gai/ha. In one embodiment, the methods utilize the benzyl ester of thecompound of formula (I) and carbendazim wherein the benzyl ester of thecompound of formula (I) is applied at a rate of from about 8 g acidequivalent per hectare (gae/ha) to about 32 gae/ha, and carbendazim isapplied at a rate of about 125 gai/ha to about 250 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with difenoconazole. With respect to the compositions, insome embodiments, the weight ratio of the compound of formula (I) orsalt or ester thereof to difenoconazole is within the range of fromabout 1:250 to about 2:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or salt or ester thereof to difenoconazoleiswithin the range of from about 1:46 to about 1:1.5. With respect to themethods, in certain embodiments, the methods comprise contacting theundesirable vegetation or locus thereof or applying to the soil or waterto prevent the emergence or growth of vegetation a composition describedherein. In some embodiments, the composition is applied at anapplication rate of from about 27 grams active ingredient per hectare(gai/ha) to about 800 gai/ha based on the total amount of activeingredients in the composition. In certain embodiments, the compositionis applied at an application rate of from about 54 grams activeingredient per hectare (gai/ha) to about 250 gai/ha based on the totalamount of active ingredients in the composition. In some embodiments,the methods comprise contacting the undesirable vegetation or locusthereof or applying to the soil or water to prevent the emergence orgrowth of vegetation with a compound of formula (I) or salt or esterthereof and difenoconazole, e.g., sequentially or simultaneously. Insome embodiments, difenoconazole is applied at a rate from about 25gai/ha to about 500 gai/ha and the compound of formula (I) of salt orester thereof is applied at a rate from about 2 gae/ha to about 300gae/ha. In some embodiments, difenoconazole is applied at a rate fromabout 50 gai/ha to about 200 gai/ha and the compound of formula (I) ofsalt or ester thereof is applied at a rate from about 8 g acidequivalent per hectare (gae/ha) to about 32 gae/ha. In certainembodiments, the methods utilize the compound of formula (I), or itsbenzyl ester and difenoconazole. In one embodiment, the methods utilizethe compound of formula (I) and difenoconazole, wherein the compound offormula (I) is applied at a rate of from about 3 g acid equivalent perhectare (gae/ha) to about 200 gae/ha, and difenoconazole is applied at arate of about 30 gai/ha to about 450 gai/ha. In one embodiment, themethods utilize the benzyl ester of the compound of formula (I) anddifenoconazole, wherein the benzyl ester of the compound of formula (I)is applied at a rate of from about 8 g acid equivalent per hectare(gae/ha) to about 32 gae/ha, and difenoconazoleis applied at a rate ofabout 50 gai/ha to about 200 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with flutolanil. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to flutolanil is within the range of from about 1:500 toabout 12:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to flutolanil is within the rangeof from about 1:70 to about 1:4. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 27 grams active ingredient per hectare (gai/ha) to about1,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 148 grams active ingredient per hectare(gai/ha) to about 592 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andflutolanil, e.g., sequentially or simultaneously. In some embodiments,flutolanil is applied at a rate from about 25 gai/ha to about 1,000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, flutolanil is applied at a rate from about 50 gai/ha toabout 900 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 3 g acid equivalent per hectare(gae/ha) to about 200 gae/ha. In certain embodiments, the methodsutilize the compound of formula (I), or its benzyl ester and flutolanil.In one embodiment, the methods utilize the compound of formula (I) andflutolanil, wherein the compound of formula (I) is applied at a rate offrom about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,and flutolanil is applied at a rate of about 50 gai/ha to about 900gai/ha. In one embodiment, the methods utilize the benzyl ester of thecompound of formula (I) and flutolanil, wherein the benzyl ester of thecompound of formula (I) is applied at a rate of from about 8 g acidequivalent per hectare (gae/ha) to about 32 gae/ha, and flutolanil isapplied at a rate of about 140 gai/ha to about 560 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with hexaconazole. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to hexaconazole is within the range of from about 1:250 toabout 60:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to hexaconazole is within the rangeof from about 1:12.5 to about 1.25:1. With respect to the methods, incertain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 7 grams active ingredient per hectare (gai/ha) to about 800gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 33 grams active ingredient per hectare(gai/ha) to about 150 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andhexaconazole, e.g., sequentially or simultaneously. In some embodiments,hexaconazole is applied at a rate from about 5 gai/ha to about 500gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, hexaconazole is applied at a rate from about 25 gai/ha toabout 100 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 8 g acid equivalent per hectare(gae/ha) to about 32 gae/ha. In certain embodiments, the methods utilizethe compound of formula (I), or its benzyl ester and hexaconazole. Inone embodiment, the methods utilize the compound of formula (I) andhexaconazole, wherein the compound of formula (I) is applied at a rateof from about 3 g acid equivalent per hectare (gae/ha) to about 200gae/ha, and hexaconazole is applied at a rate of about 7 gai/ha to about475 gai/ha. In one embodiment, the methods utilize the benzyl ester ofthe compound of formula (I) and hexaconazole, wherein the benzyl esterof the compound of formula (I) is applied at a rate of from about 8 gacid equivalent per hectare (gae/ha) to about 32 gae/ha, andhexaconazole is applied at a rate of about 25 gai/ha to about 100gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with iprobenfos. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to iprobenfosis within the range of from about 1:1,000 toabout 3:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to iprobenfos is within the rangeof from about 1:600 to about 1:1. With respect to the methods, incertain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 102 grams active ingredient per hectare (gai/ha) to about2,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 113 grams active ingredient per hectare(gai/ha) to about 1,950 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andiprobenfos, e.g., sequentially or simultaneously. In some embodiments,iprobenfos is applied at a rate from about 100 gai/ha to about 2,000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, iprobenfos is applied at a rate from about 200 gai/ha toabout 1,900 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 3 g acid equivalent per hectare(gae/ha) to about 200 gae/ha. In certain embodiments, the methodsutilize the compound of formula (I), or its benzyl ester and iprobenfos.In one embodiment, the methods utilize the compound of formula (I) andiprobenfos wherein the compound of formula (I) is applied at a rate offrom about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,and iprobenfos is applied at a rate of about 200 gai/ha to about 1,900gai/ha. In one embodiment, the methods utilize the benzyl ester of thecompound of formula (I) and iprobenfos, wherein the benzyl ester of thecompound of formula (I) is applied at a rate of from about 3 g acidequivalent per hectare (gae/ha) to about 150 gae/ha, and iprobenfosisapplied at a rate of about 110 gai/ha to about 1,800 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with isoprothiolane. With respect to the compositions, insome embodiments, the weight ratio of the compound of formula (I) orsalt or ester thereof to isoprothiolane is within the range of fromabout 1:500 to about 6:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or salt or ester thereof to isoprothiolaneis within the range of from about 1:300 to about 2:1. With respect tothe methods, in certain embodiments, the methods comprise contacting theundesirable vegetation or locus thereof or applying to the soil or waterto prevent the emergence or growth of vegetation a composition describedherein. In some embodiments, the composition is applied at anapplication rate of from about 52 grams active ingredient per hectare(gai/ha) to about 1,300 gai/ha based on the total amount of activeingredients in the composition. In certain embodiments, the compositionis applied at an application rate of from about 100 grams activeingredient per hectare (gai/ha) to about 1,100 gai/ha based on the totalamount of active ingredients in the composition. In some embodiments,the methods comprise contacting the undesirable vegetation or locusthereof or applying to the soil or water to prevent the emergence orgrowth of vegetation with a compound of formula (I) or salt or esterthereof and isoprothiolane, e.g., sequentially or simultaneously. Insome embodiments, isoprothiolane is applied at a rate from about 50gai/ha to about 1,000 gai/ha and the compound of formula (I) of salt orester thereof is applied at a rate from about 2 gae/ha to about 300gae/ha. In some embodiments, isoprothiolane is applied at a rate fromabout 75 gai/ha to about 950 gai/ha and the compound of formula (I) ofsalt or ester thereof is applied at a rate from about 3 g acidequivalent per hectare (gae/ha) to about 200 gae/ha. In certainembodiments, the methods utilize the compound of formula (I), or itsbenzyl ester and isoprothiolane. In one embodiment, the methods utilizethe compound of formula (I) and isoprothiolane, wherein the compound offormula (I) is applied at a rate of from about 3 g acid equivalent perhectare (gae/ha) to about 200 gae/ha, and isoprothiolane is applied at arate of about 75 gai/ha to about 950 gai/ha. In one embodiment, themethods utilize the benzyl ester of the compound of formula (I) andisoprothiolane, wherein the benzyl ester of the compound of formula (I)is applied at a rate of from about 3 g acid equivalent per hectare(gae/ha) to about 150 gae/ha, and isoprothiolane is applied at a rate ofabout 70 gai/ha to about 900 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with isotianil. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to isotianilis within the range of from about 1:500 toabout 30:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to isotianil is within the range offrom about 1:48 to about 1:3. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 12 grams active ingredient per hectare (gai/ha) to about1,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 108 grams active ingredient per hectare(gai/ha) to about 420 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andisotianil, e.g., sequentially or simultaneously. In some embodiments,isotianil is applied at a rate from about 10 gai/ha to about 1,000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, isotianil is applied at a rate from about 25 gai/ha toabout 380 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 8 g acid equivalent per hectare(gae/ha) to about 32 gae/ha. In certain embodiments, the methods utilizethe compound of formula (I), or its benzyl ester and isotianil. In oneembodiment, the methods utilize the compound of formula (I) andisotianil, wherein the compound of formula (I) is applied at a rate offrom about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,and isotianil is applied at a rate of about 25 gai/ha to about 700gai/ha. In one embodiment, the methods utilize the benzyl ester of thecompound of formula (I) and isotianil, wherein the benzyl ester of thecompound of formula (I) is applied at a rate of from about 8 g acidequivalent per hectare (gae/ha) to about 32 gae/ha, and isotianil isapplied at a rate of about 100 gai/ha to about 380 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with kasugamycin. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to kasugamycin is within the range of from about 1:250 toabout 150:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to kasugamycin is within the rangeof from about 1:9 to about 2:1. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 4 grams active ingredient per hectare (gai/ha) to about 800gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 25 grams active ingredient per hectare(gai/ha) to about 105 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andkasugamycin, e.g., sequentially or simultaneously. In some embodiments,kasugamycin is applied at a rate from about 2 gai/ha to about 500 gai/haand the compound of formula (I) of salt or ester thereof is applied at arate from about 2 gae/ha to about 300 gae/ha. In some embodiments,kasugamycin is applied at a rate from about 4 gai/ha to about 450 gai/haand the compound of formula (I) of salt or ester thereof is applied at arate from about 3 g acid equivalent per hectare (gae/ha) to about 200gae/ha. In certain embodiments, the methods utilize the compound offormula (I), or its benzyl ester and kasugamycin. In one embodiment, themethods utilize the compound of formula (I) and kasugamycin wherein thecompound of formula (I) is applied at a rate of from about 3 g acidequivalent per hectare (gae/ha) to about 200 gae/ha, and kasugamycin isapplied at a rate of about 4 gai/ha to about 450 gai/ha. In oneembodiment, the methods utilize the benzyl ester of the compound offormula (I) and kasugamycin, wherein the benzyl ester of the compound offormula (I) is applied at a rate of from about 8 g acid equivalent perhectare (gae/ha) to about 32 gae/ha, and kasugamycin is applied at arate of about 17.5 gai/ha to about 70 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with mancozeb. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to mancozeb is within the range of from about 1:2,500 toabout 12:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to mancozebis within the range offrom about 1:210 to about 1:26. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 27 grams active ingredient per hectare (gai/ha) to about5,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 848 grams active ingredient per hectare(gai/ha) to about 1,712 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andmancozeb, e.g., sequentially or simultaneously. In some embodiments,mancozebis applied at a rate from about 25 gai/ha to about 5,000 gai/haand the compound of formula (I) of salt or ester thereof is applied at arate from about 2 gae/ha to about 300 gae/ha. In some embodiments,mancozeb is applied at a rate from about 50 gai/ha to about 4,500 gai/haand the compound of formula (I) of salt or ester thereof is applied at arate from about 3 g acid equivalent per hectare (gae/ha) to about 200gae/ha. In certain embodiments, the methods utilize the compound offormula (I), or its benzyl ester and mancozeb. In one embodiment, themethods utilize the compound of formula (I) and mancozeb, wherein thecompound of formula (I) is applied at a rate of from about 3 g acidequivalent per hectare (gae/ha) to about 200 gae/ha, and mancozeb isapplied at a rate of about 50 gai/ha to about 4,500 gai/ha. In oneembodiment, the methods utilize the benzyl ester of the compound offormula (I) and mancozeb, wherein the benzyl ester of the compound offormula (I) is applied at a rate of from about 8 g acid equivalent perhectare (gae/ha) to about 32 gae/ha, and mancozeb is applied at a rateof about 840 gai/ha to about 1,680 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with myclobutanil. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to myclobutanil is within the range of from about 1:250 toabout 12:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to myclobutanil is within the rangeof from about 1:38 to about 1:1.5. With respect to the methods, incertain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 22 grams active ingredient per hectare (gai/ha) to about 800gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 55 grams active ingredient per hectare(gai/ha) to about 232 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andmyclobutanil, e.g., sequentially or simultaneously. In some embodiments,myclobutanil is applied at a rate from about 25 gai/ha to about 500gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, myclobutanil is applied at a rate from about 50 gai/ha toabout 200 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 5 g acid equivalent per hectare(gae/ha) to about 32 gae/ha. In certain embodiments, the methods utilizethe compound of formula (I), or its benzyl ester and myclobutanil. Inone embodiment, the methods utilize the compound of formula (I) andmyclobutanil, wherein the compound of formula (I) is applied at a rateof from about 3 g acid equivalent per hectare (gae/ha) to about 200gae/ha, and myclobutanil is applied at a rate of about 50 gai/ha toabout 450 gai/ha. In one embodiment, the methods utilize the benzylester of the compound of formula (I) and myclobutanil, wherein thebenzyl ester of the compound of formula (I) is applied at a rate of fromabout 5 g acid equivalent per hectare (gae/ha) to about 32 gae/ha, andmyclobutanil is applied at a rate of about 50 gai/ha to about 200gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with phthalide. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to phthalide is within the range of from about 1:500 toabout 15:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to phthalide is within the range offrom about 1:267 to about 5:1. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 22 grams active ingredient per hectare (gai/ha) to about1,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 33 grams active ingredient per hectare(gai/ha) to about 950 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andphthalide, e.g., sequentially or simultaneously. In some embodiments,phthalide is applied at a rate from about 20 gai/ha to about 1,000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, phthalide is applied at a rate from about 25 gai/ha toabout 950 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 3 g acid equivalent per hectare(gae/ha) to about 200 gae/ha. In certain embodiments, the methodsutilize the compound of formula (I), or its benzyl ester and phthalide.In one embodiment, the methods utilize the compound of formula (I) andphthalide, wherein the compound of formula (I) is applied at a rate offrom about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,and phthalide is applied at a rate of about 25 gai/ha to about 950gai/ha. In one embodiment, the methods utilize the benzyl ester of thecompound of formula (I) and phthalide, wherein the benzyl ester of thecompound of formula (I) is applied at a rate of from about 3 g acidequivalent per hectare (gae/ha) to about 150 gae/ha, and phthalide isapplied at a rate of about 30 gai/ha to about 800 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with probenazole. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to probenazoleis within the range of from about 1:2,500 toabout 6:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to probenazoleis within the rangeof from about 1:500 to about 1:10. With respect to the methods, incertain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 52 grams active ingredient per hectare (gai/ha) to about5,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 103 grams active ingredient per hectare(gai/ha) to about 4,050 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andprobenazole, e.g., sequentially or simultaneously. In some embodiments,probenazole is applied at a rate from about 50 gai/ha to about 5,000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, probenazole is applied at a rate from about 75 gai/ha toabout 4,500 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 3 g acid equivalent per hectare(gae/ha) to about 200 gae/ha. In certain embodiments, the methodsutilize the compound of formula (I), or its benzyl ester andprobenazole. In one embodiment, the methods utilize the compound offormula (I) and probenazole, wherein the compound of formula (I) isapplied at a rate of from about 3 g acid equivalent per hectare (gae/ha)to about 200 gae/ha, and probenazoleis applied at a rate of about 75gai/ha to about 4,500 gai/ha. In one embodiment, the methods utilize thebenzyl ester of the compound of formula (I) and probenazole wherein thebenzyl ester of the compound of formula (I) is applied at a rate of fromabout 8 g acid equivalent per hectare (gae/ha) to about 50 gae/ha, andprobenazoleis applied at a rate of about 500 gai/ha to about 4,000gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with propiconazole. With respect to the compositions, insome embodiments, the weight ratio of the compound of formula (I) orsalt or ester thereof to propiconazole is within the range of from about1:250 to about 30:1. In certain embodiments, the weight ratio of thecompound of formula (I) or salt or ester thereof to propiconazole iswithin the range of from about 1:47 to about 1:3. With respect to themethods, in certain embodiments, the methods comprise contacting theundesirable vegetation or locus thereof or applying to the soil or waterto prevent the emergence or growth of vegetation a composition describedherein. In some embodiments, the composition is applied at anapplication rate of from about 12 grams active ingredient per hectare(gai/ha) to about 800 gai/ha based on the total amount of activeingredients in the composition. In certain embodiments, the compositionis applied at an application rate of from about 67 grams activeingredient per hectare (gai/ha) to about 275 gai/ha based on the totalamount of active ingredients in the composition. In some embodiments,the methods comprise contacting the undesirable vegetation or locusthereof or applying to the soil or water to prevent the emergence orgrowth of vegetation with a compound of formula (I) or salt or esterthereof and propiconazole, e.g., sequentially or simultaneously. In someembodiments, propiconazole is applied at a rate from about 10 gai/ha toabout 500 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. Insome embodiments, propiconazole is applied at a rate from about 20gai/ha to about 450 gai/ha and the compound of formula (I) of salt orester thereof is applied at a rate from about 3 g acid equivalent perhectare (gae/ha) to about 200 gae/ha. In certain embodiments, themethods utilize the compound of formula (I), or its benzyl ester andpropiconazole. In one embodiment, the methods utilize the compound offormula (I) and propiconazole, wherein the compound of formula (I) isapplied at a rate of from about 3 g acid equivalent per hectare (gae/ha)to about 200 gae/ha, and propiconazole is applied at a rate of about 20gai/ha to about 450 gai/ha. In one embodiment, the methods utilize thebenzyl ester of the compound of formula (I) and propiconazole, whereinthe benzyl ester of the compound of formula (I) is applied at a rate offrom about 5.3 g acid equivalent per hectare (gae/ha) to about 21.2gae/ha, and propiconazole is applied at a rate of about 62.5 gai/ha toabout 250 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with pyroquilon. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to pyroquilon is within the range of from about 1:1,500 toabout 3:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to pyroquilon is within the rangeof from about 1:933 to about 1:1. With respect to the methods, incertain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 102 grams active ingredient per hectare (gai/ha) to about3,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 153 grams active ingredient per hectare(gai/ha) to about 2,950 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andpyroquilon, e.g., sequentially or simultaneously. In some embodiments,pyroquilon is applied at a rate from about 100 gai/ha to about 3,000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, pyroquilon is applied at a rate from about 75 gai/ha toabout 2,900 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 3 g acid equivalent per hectare(gae/ha) to about 200 gae/ha. In certain embodiments, the methodsutilize the compound of formula (I), or its benzyl ester and pyroquilon.In one embodiment, the methods utilize the compound of formula (I) andpyroquilon, wherein the compound of formula (I) is applied at a rate offrom about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,and pyroquilon is applied at a rate of about 75 gai/ha to about 2,900gai/ha. In one embodiment, the methods utilize the benzyl ester of thecompound of formula (I) and pyroquilon wherein the benzyl ester of thecompound of formula (I) is applied at a rate of from about 3 g acidequivalent per hectare (gae/ha) to about 150 gae/ha, and pyroquilon isapplied at a rate of about 150 gai/ha to about 2,800 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with tebuconazole. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to tebuconazole is within the range of from about 1:250 toabout 12:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to tebuconazole is within the rangeof from about 1:57 to about 1:2. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 27 grams active ingredient per hectare (gai/ha) to about5,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 66 grams active ingredient per hectare(gai/ha) to about 280 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andtebuconazole, e.g., sequentially or simultaneously. In some embodiments,tebuconazole is applied at a rate from about 25 gai/ha to about 5,000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, tebuconazole is applied at a rate from about 60 gai/ha toabout 250 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 4 g acid equivalent per hectare(gae/ha) to about 32 gae/ha. In certain embodiments, the methods utilizethe compound of formula (I), or its benzyl ester and tebuconazole. Inone embodiment, the methods utilize the compound of formula (I) andtebuconazole, wherein the compound of formula (I) is applied at a rateof from about 3 g acid equivalent per hectare (gae/ha) to about 200gae/ha, and tebuconazole is applied at a rate of about 50 gai/ha toabout 450 gai/ha. In one embodiment, the methods utilize the benzylester of the compound of formula (I) and tebuconazole, wherein thebenzyl ester of the compound of formula (I) is applied at a rate of fromabout 4 g acid equivalent per hectare (gae/ha) to about 32 gae/ha, andtebuconazole is applied at a rate of about 60 gai/ha to about 250gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with thifluzamide. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to thifluzamide is within the range of from about 1:375 toabout 30:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to thifluzamide is within the rangeof from about 1:38 to about 1:2.5. With respect to the methods, incertain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 12 grams active ingredient per hectare (gai/ha) to about1,050 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 83 grams active ingredient per hectare(gai/ha) to about 332 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andthifluzamide, e.g., sequentially or simultaneously. In some embodimentsthifluzamide is applied at a rate from about 10 gai/ha to about 750gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, thifluzamide is applied at a rate from about 20 gai/ha toabout 700 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 3 g acid equivalent per hectare(gae/ha) to about 200 gae/ha. In certain embodiments, the methodsutilize the compound of formula (I), or its benzyl ester andthifluzamide. In one embodiment, the methods utilize the compound offormula (I) and thifluzamide, wherein the compound of formula (I) isapplied at a rate of from about 3 g acid equivalent per hectare (gae/ha)to about 200 gae/ha, and thifluzamide is applied at a rate of about 20gai/ha to about 700 gai/ha. In one embodiment, the methods utilize thebenzyl ester of the compound of formula (I) and thifluzamide, whereinthe benzyl ester of the compound of formula (I) is applied at a rate offrom about 8 g acid equivalent per hectare (gae/ha) to about 32 gae/ha,and thifluzamide is applied at a rate of about 75 gai/ha to about 300gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with tricyclazole. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to tricyclazole is within the range of from about 1:375 toabout 15:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to tricyclazole is within the rangeof from about 1:170 to about 1:1. With respect to the methods, incertain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 22 grams active ingredient per hectare (gai/ha) to about1,300 gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 55 grams active ingredient per hectare(gai/ha) to about 800 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andtricyclazole, e.g., sequentially or simultaneously. In some embodiments,tricyclazole is applied at a rate from about 20 gai/ha to about 1,000gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, tricyclazole is applied at a rate from about 30 gai/ha toabout 750 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 4 g acid equivalent per hectare(gae/ha) to about 42 gae/ha. In certain embodiments, the methods utilizethe compound of formula (I), or its benzyl ester and tricyclazole. Inone embodiment, the methods utilize the compound of formula (I) andtricyclazole, wherein the compound of formula (I) is applied at a rateof from about 3 g acid equivalent per hectare (gae/ha) to about 200gae/ha, and tricyclazole is applied at a rate of about 30 gai/ha toabout 950 gai/ha. In one embodiment, the methods utilize the benzylester of the compound of formula (I) and tricyclazole, wherein thebenzyl ester of the compound of formula (I) is applied at a rate of fromabout 4.4 g acid equivalent per hectare (gae/ha) to about 42.4 gae/ha,and tricyclazole is applied at a rate of about 50 gai/ha to about 750gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with trifloxystrobin. With respect to the compositions, insome embodiments, the weight ratio of the compound of formula (I) orsalt or ester thereof to trifloxystrobin is within the range of fromabout 1:250 to about 30:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or salt or ester thereof to trifloxystrobinis within the range of from about 1:38 to about 1:2. With respect to themethods, in certain embodiments, the methods comprise contacting theundesirable vegetation or locus thereof or applying to the soil or waterto prevent the emergence or growth of vegetation a composition describedherein. In some embodiments, the composition is applied at anapplication rate of from about 12 grams active ingredient per hectare(gai/ha) to about 800 gai/ha based on the total amount of activeingredients in the composition. In certain embodiments, the compositionis applied at an application rate of from about 83 grams activeingredient per hectare (gai/ha) to about 332 gai/ha based on the totalamount of active ingredients in the composition. In some embodiments,the methods comprise contacting the undesirable vegetation or locusthereof or applying to the soil or water to prevent the emergence orgrowth of vegetation with a compound of formula (I) or salt or esterthereof and trifloxystrobin, e.g., sequentially or simultaneously. Insome embodiments, trifloxystrobinis applied at a rate from about 10gai/ha to about 500 gai/ha and the compound of formula (I) of salt orester thereof is applied at a rate from about 2 gae/ha to about 300gae/ha. In some embodiments, trifloxystrobin is applied at a rate fromabout 20 gai/ha to about 450 gai/ha and the compound of formula (I) ofsalt or ester thereof is applied at a rate from about 3 g acidequivalent per hectare (gae/ha) to about 200 gae/ha. In certainembodiments, the methods utilize the compound of formula (I), or itsbenzyl ester and trifloxystrobin. In one embodiment, the methods utilizethe compound of formula (I) and trifloxystrobin, wherein the compound offormula (I) is applied at a rate of from about 3 g acid equivalent perhectare (gae/ha) to about 200 gae/ha, and trifloxystrobin is applied ata rate of about 20 gai/ha to about 450 gai/ha. In one embodiment, themethods utilize the benzyl ester of the compound of formula (I) andtrifloxystrobin, wherein the benzyl ester of the compound of formula (I)is applied at a rate of from about 8 g acid equivalent per hectare(gae/ha) to about 32 gae/ha, and trifloxystrobin is applied at a rate ofabout 75 gai/ha to about 300 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with validamycin. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to validamycin is within the range of from about 1:25 toabout 3,000:1. In certain embodiments, the weight ratio of the compoundof formula (I) or salt or ester thereof to validamycin is within therange of from about 1:13 to about 500:1. With respect to the methods, incertain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 2.1 grams active ingredient per hectare (gai/ha) to about 350gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 3.3 grams active ingredient per hectare(gai/ha) to about 190 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andvalidamycin, e.g., sequentially or simultaneously. In some embodiments,validamycin is applied at a rate from about 0.1 gai/ha to about 50gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, validamycin is applied at a rate from about 0.2 gai/ha toabout 45 gai/ha and the compound of formula (I) of salt or ester thereofis applied at a rate from about 3 g acid equivalent per hectare (gae/ha)to about 200 gae/ha. In certain embodiments, the methods utilize thecompound of formula (I), or its benzyl ester and validamycin. In oneembodiment, the methods utilize the compound of formula (I) andvalidamycin, wherein the compound of formula (I) is applied at a rate offrom about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,and validamycin is applied at a rate of about 0.2 gai/ha to about 45gai/ha. In one embodiment, the methods utilize the benzyl ester of thecompound of formula (I) and validamycin, wherein the benzyl ester of thecompound of formula (I) is applied at a rate of from about 3 g acidequivalent per hectare (gae/ha) to about 150 gae/ha, and validamycin isapplied at a rate of about 0.3 gai/ha to about 40 gai/ha.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with a compound of formula (II). With respect to thecompositions, in some embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to a compound of formula (II) iswithin the range of from about 1:375 to about 150:1. In certainembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to a compound of formula (II) is within the range of fromabout 1:19 to about 1:1. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate offrom about 4 grams active ingredient per hectare (gai/ha) to about 1,050gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate of from about 45 grams active ingredient per hectare(gai/ha) to about 182 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof and acompound of formula (II), e.g., sequentially or simultaneously. In someembodiments, a compound of formula (II) is applied at a rate from about2 gai/ha to about 750 gai/ha and the compound of formula (I) of salt orester thereof is applied at a rate from about 2 gae/ha to about 300gae/ha. In some embodiments, a compound of formula (II) is applied at arate from about 5 gai/ha to about 700 gai/ha and the compound of formula(I) of salt or ester thereof is applied at a rate from about 3 g acidequivalent per hectare (gae/ha) to about 200 gae/ha. In certainembodiments, the methods utilize the compound of formula (I), or itsbenzyl ester and a compound of formula (II). In one embodiment, themethods utilize the compound of formula (I) and a compound of formula(II), wherein the compound of formula (I) is applied at a rate of fromabout 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha, anda compound of formula (II) is applied at a rate of about 5 gai/ha toabout 700 gai/ha. In one embodiment, the methods utilize the benzylester of the compound of formula (I) and a compound of formula (II),wherein the benzyl ester of the compound of formula (I) is applied at arate of from about 8 g acid equivalent per hectare (gae/ha) to about 32gae/ha, and a compound of formula (II) is applied at a rate of about37.5 gai/ha to about 180 gai/ha.

In certain embodiments, the methods and compositions utilizing thecompound of formula (I) or salt or ester thereof in combination withazoxystrobin, carbendazim, difenoconazole, flutolanil, hexaconazole,iprobenfos, isoprothiolane, isotianil, kasugamycin, mancozeb,myclobutanil, phthalide, probenazole, propiconazole, pyroquilon,tebuconazole, thifluzamide, tricyclazole, trifloxystrobin, validamycin,and a compound of formula (II) are used to control BRAPP, CYPES, CYPIR,CYPRO, DIGSA, ECHCG, ECHCO, ECHOR, FIMMI, IPOHE, LEFCH and SCPJU.

The components of the mixtures described herein can be applied eitherseparately or as part of a multipart herbicidal system.

The mixtures described herein can be applied in conjunction with one ormore other herbicides to control a wider variety of undesirablevegetation. When used in conjunction with other herbicides, thecomposition can be formulated with the other herbicide or herbicides,tank mixed with the other herbicide or herbicides or appliedsequentially with the other herbicide or herbicides. Some of theherbicides that can be employed in conjunction with the compositions andmethods described herein include, but are not limited to: 4-CPA; 4-CPB;4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB;3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB;acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor,alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin,amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid,amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron,asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne,barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin,benfuresate, bensulfuron-methyl, bensulide, benthiocarb,bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon,benzofenap, benzofluor, benzoylprop, benzthiazuron, bialaphos,bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil,bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon,butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron,butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole,calcium chlorate, calcium cyanamide, cambendichlor, carbasulam,carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC,chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine,chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop,chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen,chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham,chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin,cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop-propargyl,clofop, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl,CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron,cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron,cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole,cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn,di-allate, dicamba, dichlobenil, dichloralurea, dichlormate,dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, diethamquat,diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine,dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid,dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP,eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin,ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid,etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen,etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop,fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone,fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate,flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop,fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron,fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam,flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron,fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron,flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurtamone,fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen,glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosatesalts and esters, halauxifen, halauxifen-methyl, halosafen,halosulfuron-methyl, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl,hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox,imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, indanofan,indaziflam, iodobonil, iodomethane, iodosulfuron,iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine,ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin,isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben,isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox,lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines,MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet,mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop,metamitron, metazachlor, metazosulfuron, metflurazon,methabenzthiazuron, methalpropalin, methazole, methiobencarb,methiozolin, methiuron, methometon, methoprotryne, methyl bromide,methyl isothiocyanate, methyldymron, metobenzuron, metobromuron,metolachlor, metosulam, metoxuron, metribuzin, metsulfuron,metsulfuron-methyl, molinate, monalide, monisouron, monochloroaceticacid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide,naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen,nitrofluorfen, norflurazon, noruron, OCH, orbencarb,ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon,oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl,parafluoron, paraquat, pebulate, pelargonic acid, pendimethalin,penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone,pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl,phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden,piperophos, potassium arsenite, potassium azide, potassium cyanate,pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol,profluralin, profoxydim, proglinazine, prohexadione-calcium, prometon,prometryn, pronamide, propachlor, propanil, propaquizafop, propazine,propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide,prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon,pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate,pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor,pyridafol, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil,rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton,sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite,sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone,sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin,SYN-523, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,terbuthylazine, terbutryn, tetrafluoron, thenylchlor, thiazafluoron,thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl,thifensulfuron, thifensulfurn-methyl, thiobencarb, tiocarbazil,tioclorim, topramezone, tralkoxydim, triafamone, tri-allate,triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba,triclopyr choline salt, triclopyr esters and amines, tridiphane,trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop,trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritactritosulfuron, vernolate, xylachlor and salts, esters, optically activeisomers and mixtures thereof.

The compositions and methods described herein, can further be used inconjunction with glyphosate, 5-enolpyruvylshikimate-3-phosphate (EPSP)synthase inhibitors, glufosinate, glutamine synthetase inhibitors,dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxintransport inhibitors, aryloxyphenoxypropionates, cyclohexanediones,phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors,imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,triazolopyrimidines, sulfonylaminocarbonyltriazolinones, acetolactatesynthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoenedesaturase inhibitors, carotenoid biosynthesis inhibitors,protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesisinhibitors, mitosis inhibitors, microtubule inhibitors, very long chainfatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors,photosystem I inhibitors, photosystem II inhibitors, triazines, andbromoxynil on glyphosate-tolerant, EPSP synthase inhibitor-tolerant,glufosinate-tolerant, glutamine synthetase inhibitor-tolerant,dicamba-tolerant, phenoxy auxin-tolerant, pyridyloxy auxin-tolerant,auxin-tolerant, auxin transport inhibitor-tolerant,aryloxyphenoxypropionate-tolerant, cyclohexanedione-tolerant,phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinone-tolerant,sulfonylurea-tolerant, pyrimidinylthiobenzoate-tolerant,triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant,ALS— or AHAS-tolerant, HPPD-tolerant, phytoene desaturaseinhibitor-tolerant, carotenoid biosynthesis inhibitor tolerant,PPO-tolerant, cellulose biosynthesis inhibitor-tolerant, mitosisinhibitor-tolerant, microtubule inhibitor-tolerant, very long chainfatty acid inhibitor-tolerant, fatty acid and lipid biosynthesisinhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem IIinhibitor-tolerant, triazine-tolerant, bromoxynil-tolerant, and cropspossessing multiple or stacked traits conferring tolerance to multiplechemistries and/or multiple modes of action via single and/or multipleresistance mechanisms. In some embodiments, the compound of formula (I)or salt or ester thereof and complementary herbicide or salt or esterthereof are used in combination with herbicides that are selective forthe crop being treated and which complement the spectrum of weedscontrolled by these compounds at the application rate employed. In someembodiments, the compositions described herein and other complementaryherbicides are applied at the same time, either as a combinationformulation or as a tank mix.

In some embodiments, the compositions described herein are employed incombination with one or more herbicide safeners, such as AD-67 (MON4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl),cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton,fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole,harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi,mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil,R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance theirselectivity. In some embodiments, the safeners are employed in rice,cereal, corn, or maize settings. In some embodiments, the safener iscloquintocet or an ester or salt thereof. In certain embodiments,cloquintocet is utilized to antagonize harmful effects of thecompositions on rice and cereals. In some embodiments, the safener iscloquintocet (mexyl).

In some embodiments, the compositions described herein are employed incombination with one or more plant growth regulators, such as2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide,α-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl alcohol,kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron,tribufos, aviglycine, maleic hydrazide, gibberellins, gibberellic acid,abscisic acid, ancymidol, fosamine, glyphosine, isopyrimol, jasmonicacid, maleic hydrazide, mepiquat, 2,3,5-tri-iodobenzoic acid,morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol,tetcyclacis, uniconazole, brassinolide, brassinolide-ethyl,cycloheximide, ethylene, methasulfocarb, prohexadione, triapenthenol andtrinexapac.

In some embodiments, the plant growth regulators are employed in one ormore crops or settings, such as rice, cereal crops, corn, maize,broadleaf crops, oilseed rape/canola, turf, pineapple, sugarcane,sunflower, pastures, grasslands, rangelands, fallowland, tree and vineorchards, plantation crops, vegetables, and non-crop (ornamentals)settings. In some embodiments, the plant growth regulator is mixed withthe compound of formula (I), or mixed with the compound of formula (I)and fungicides to cause a preferentially advantageous effect on plants.

In some embodiments, compositions provided herein further comprise atleast one agriculturally acceptable adjuvant or carrier. Suitableadjuvants or carriers should not be phytotoxic to valuable crops,particularly at the concentrations employed in applying the compositionsfor selective weed control in the presence of crops, and should notreact chemically with herbicidal components or other compositioningredients. Such mixtures can be designed for application directly toweeds or the area adjacent to the weeds or can be concentrates orformulations that are normally diluted with additional carriers andadjuvants before application. They can be solids, such as, for example,dusts, granules, water-dispersible granules, or wettable powders, orliquids, such as, for example, emulsifiable concentrates, solutions,emulsions or suspensions. They can also be provided as a pre-mix or tankmixed.

Suitable agricultural adjuvants and carriers include, but are notlimited to, crop oil concentrate; nonylphenol ethoxylate;benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleumhydrocarbon, alkyl esters, organic acid, and anionic surfactant; C₉-C₁₁alkylpolyglycoside; phosphated alcohol ethoxylate; natural primaryalcohol (C₁₂-C₁₆) ethoxylate; di-sec-butylphenol EO-PO block copolymer;polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrate;emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate(8EO); tallow amine ethoxylate (15 EO); PEG (400) dioleate-99.

Liquid carriers that can be employed include water and organic solvents.The organic solvents include, but are not limited to, petroleumfractions or hydrocarbons such as mineral oil, aromatic solvents,paraffinic oils, and the like; vegetable oils such as soybean oil,rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil,corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, saffloweroil, sesame oil, tung oil and the like; esters of the above vegetableoils; esters of monoalcohols or dihydric, trihydric, or other lowerpolyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate,n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octylsuccinate, di-butyl adipate, di-octyl phthalate and the like; esters ofmono, di and polycarboxylic acids and the like. Specific organicsolvents include, but are not limited to toluene, xylene, petroleumnaphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone,trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butylacetate, propylene glycol monomethyl ether and diethylene glycolmonomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amylalcohol, ethylene glycol, propylene glycol, glycerine,N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide,liquid fertilizers and the like. In certain embodiments, water is thecarrier for the dilution of concentrates.

Suitable solid carriers include but are not limited to talc,pyrophillite clay, silica, attapulgus clay, kaolin clay, kieselguhr,chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay,Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice,wood flour, walnut shell flour, lignin, cellulose, and the like.

In some embodiments, the compositions described herein further compriseone or more surface-active agents. In some embodiments, suchsurface-active agents are employed in both solid and liquidcompositions, and in certain embodiments those designed to be dilutedwith carrier before application. The surface-active agents can beanionic, cationic or nonionic in character and can be employed asemulsifying agents, wetting agents, suspending agents, or for otherpurposes. Surfactants which may also be used in the present formulationsare described, inter alia, in “McCutcheon's Detergents and EmulsifiersAnnual,” MC Publishing Corp., Ridgewood, N.J., 1998 and in “Encyclopediaof Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980-81.Surface-active agents include, but are not limited to salts of alkylsulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonatesalts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkyleneoxide addition products, such as nonylphenol-C₁₈ ethoxylate;alcohol-alkylene oxide addition products, such as tridecyl alcohol-C₁₆ethoxylate; soaps, such as sodium stearate; alkyl-naphthalene-sulfonatesalts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters ofsulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate;sorbitol esters, such as sorbitol oleate; quaternary amines, such aslauryl trimethylammonium chloride; polyethylene glycol esters of fattyacids, such as polyethylene glycol stearate; block copolymers ofethylene oxide and propylene oxide; salts of mono and dialkyl phosphateesters; vegetable or seed oils such as soybean oil, rapeseed/canola oil,olive oil, castor oil, sunflower seed oil, coconut oil, corn oil,cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesameoil, tung oil and the like; and esters of the above vegetable oils, andin certain embodiments, methyl esters.

In some embodiments, these materials, such as vegetable or seed oils andtheir esters, can be used interchangeably as an agricultural adjuvant,as a liquid carrier or as a surface active agent.

Other exemplary additives for use in the compositions provided hereininclude but are not limited to compatibilizing agents, antifoam agents,sequestering agents, neutralizing agents and buffers, corrosioninhibitors, dyes, odorants, spreading agents, penetration aids, stickingagents, dispersing agents, thickening agents, freezing pointdepressants, antimicrobial agents, and the like. The compositions mayalso contain other compatible components, for example, other herbicides,plant growth regulants, fungicides, fungicides, and the like and can beformulated with liquid fertilizers or solid, particulate fertilizercarriers such as ammonium nitrate, urea and the like.

In some embodiments, the concentration of the active ingredients in thecompositions described herein is from about 0.0005 to 98 percent byweight. In some embodiments, the concentration is from about 0.0006 to90 percent by weight. In compositions designed to be employed asconcentrates, the active ingredients, in certain embodiments, arepresent in a concentration from about 0.1 to 98 weight percent, and incertain embodiment's about 0.5 to 90 weight percent. Such compositionsare, in certain embodiments, diluted with an inert carrier, such aswater, before application. The diluted compositions usually applied toweeds or the locus of weeds contain, in certain embodiments, about0.0006 to 25.0 weight percent active ingredient and in certainembodiments contain about 0.001 to 20.0 weight percent.

The present compositions can be applied to undesirable vegetation(weeds) or the area adjacent to the weeds by the use of conventionalground or aerial dusters, sprayers, and granule applicators, by additionto irrigation or paddy water, and by other conventional means known tothose skilled in the art.

The described embodiments and following examples are for illustrativepurposes and are not intended to limit the scope of the claims. Othermodifications, uses, or combinations with respect to the compositionsdescribed herein will be apparent to a person of ordinary skill in theart without departing from the spirit and scope of the claimed subjectmatter.

EXAMPLES

Results in Examples I and II are greenhouse trial results.

Example I Evaluation of Postemergence Foliar-Applied Herbicidal Mixturesfor Weed Control in Direct-Seeded Rice

Seeds or nutlets of the desired test plant species were planted in asoil matrix prepared by mixing aloam or sandy loam soil (e.g., 28.6percent silt, 18.8 percent clay, and 52.6 percent sand, with a pH ofabout 5.8 and an organic matter content of about 1.8 percent) andcalcareous grit in an 80 to 20 ratio. The soil matrix was contained inplastic pots with a volume of 1 quart and a surface area of 83.6 cm².When required to ensure good germination and healthy plants, a fungicidetreatment and/or other chemical or physical treatment was applied. Theplants were grown for 8-22 days in a greenhouse with an approximate 14 hphotoperiod which was maintained at about 29° C. during the day and 26°C. during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and ironchelate) were applied in the irrigation solution as needed and water wasadded on a regular basis. Supplemental lighting was provided withoverhead metal halide 1000-Watt lamps as necessary. The plants wereemployed for testing when they reached the first through fourth trueleaf stage.

Treatments consisted of the acid or esters of4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylicacid (Compound A), each formulated as an SC (suspension concentrate),and various fungicidal components alone and in combination. Forms ofcompound A were applied on an acid equivalent basis.

Forms of compound A (compound of formula I) tested include:

.Other fungicidal components were applied on an active ingredient basisand consisted of azoxystrobin formulated as Amistar®, carbendazim(technical grade material), difenoconazole formulated as Inspire®,flutolanil (technical grade material), hexaconazole (technical gradematerial), isotianil (technical grade material), kasugamycin (technicalgrade material), mancozeb formulated as Dithane® M45, myclobutanilformulated as Eagle®, propiconazole formulated as Tilt®, tebuconazoleformulated as Corail®, thifluzamide (technical grade material),tricyclazole formulated as Beam®, trifloxystrobin (technical gradematerial), and a compound of formula (II) formulated as an SC.

Treatment requirements were calculated based upon the rates beingtested, the concentration of active ingredient or acid equivalent in theformulation, and a 12 mL application volume at a rate of 187 L/ha.

For treatments comprised of technical compounds, weighed amounts can beplaced individually in 25 mL glass vials and dissolved in a volume of97:3 v/v acetone/DMSO to obtain 12× stock solutions. If a test compounddoes not dissolve readily, the mixture can be warmed and/or sonicated.Application solutions can be prepared by adding an appropriate amount ofeach stock solution (e.g., 1 mL) and diluted to the appropriate finalconcentrations with the addition of 10 mL of an aqueous mixture of 1.5%(v/v) crop oil concentrate so that the final spray solutions contain1.25% (v/v) crop oil concentrate. When technical materials are used, theconcentrated stock solutions can be added to the spray solutions so thatthe final acetone and DMSO concentrations of the application solutionsare 16.2% and 0.5%, respectively.

For treatments comprised of formulated and technical compounds, weighedamounts of the technical materials can be placed individually in 25 mLglass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain12× stock solutions, and measured amounts of the formulated compoundscan be placed individually in 25 mL glass vials and diluted in a volumeof 1.5% (v/v) crop oil concentrate or water to obtain 12× stocksolutions. If a test compound does not dissolve readily, the mixture canbe warmed and/or sonicated. Application solutions can be prepared byadding an appropriate amount of each stock solution (e.g., 1 mL) anddiluted to the appropriate final concentrations with the addition of anappropriate amount of an aqueous mixture of 1.5% (v/v) crop oilconcentrate so that the final spray solutions contain 1.25% (v/v) cropoil concentrate. As required, additional water and/or 97:3 v/vacetone/DMSO can be added to individual application solutions so thatthe final acetone and DMSO concentrations of the application solutionsbeing compared are 8.1% and 0.25%, respectively

All stock solutions and applications solutions were visually inspectedfor compound compatibility prior to application. Spray solutions wereapplied to the plant material with an overhead Mandel track sprayerequipped with a 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 m² at a spray height of 18 to 20 inches (46 to50 cm) above average plant canopy height. Control plants were sprayed inthe same manner with the solvent blank.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After approximately 3 weeks, the condition of the testplants as compared with that of the untreated plants was determinedvisually and scored on a scale of 0 to 100 percent where 0 correspondsto no injury or growth inhibition and 100 corresponds to complete kill.

Colby's equation was used to determine the herbicidal effects expectedfrom the mixtures (Colby, S. R. 1967. Calculation of the synergistic andantagonistic response of herbicide combinations. Weeds 15:20-22).

The following equation was used to calculate the expected activity ofmixtures containing two active ingredients, A and B:Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration asused in the mixture.

B=observed efficacy of active ingredient B at the same concentration asused in the mixture.

The compounds tested, application rates employed, plant species tested,and results are given in Tables 1-22.

TABLE 1 Synergistic Activity of Foliar-Applied Compound A Acid andAzoxystrobin Compositions on Weed Control in a Rice Cropping System.Compound A Visual Weed Control (%) - 21 DAA Acid Azoxystrobin DIGSAIPOHE gae/ha gai/ha Obs Exp Obs Exp 5.3 0 10 — 10 — 10.6 0 20 — 15 —21.2 0 20 — 20 — 0 250 0 — 0 — 5.3 250 30 10 20 10 10.6 250 25 20 30 1521.2 250 NT 20 25 20

TABLE 2 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Azoxystrobin Compositions on Weed Control in a Rice Cropping System.Compound A Visual Weed Control (%) - 21 DAA Benzyl Ester AzoxystrobinDIGSA IPOHE gae/ha gai/ha Obs Exp Obs Exp 4.38 0 20 — 10 — 8.75 0 15 —10 — 17.5 0 20 — 20 — 0 250 0 — 0 — 4.38 250 20 20 25 10 8.75 250 60 1515 10 17.5 250 50 20 30 20 Compound A Visual Weed Control (%) - 22 DAABenzyl Ester Azoxystrobin CYPIR gae/ha gai/ha Obs Exp 16 0 73 — 32 0 60— 0 62.5 0 — 0 125 0 — 0 250 0 — 16 62.5 100 73 32 62.5 100 60 16 125 8573 32 125 100 60 16 250 98 73 32 250 100 60 Compound A Visual WeedControl (%) - 22 DAA Benzyl Ester Azoxystrobin BRAPP gae/ha gai/ha ObsExp 8 0 65 — 16 0 70 — 32 0 90 — 0 125 0 — 0 250 0 — 8 125 70 65 16 12573 70 32 125 90 90 8 250 78 65 16 250 83 70 32 250 90 90 Compound AVisual Weed Control (%) - 21 DAA Benzyl Ester Azoxystrobin ECHOR gae/hagai/ha Obs Exp 16 0 43 — 32 0 70 — 0 62.5 8 — 0 125 8 — 0 250 5 — 1662.5 40 47 32 62.5 85 72 16 125 58 47 32 125 90 72 16 250 58 45 32 25090 72

TABLE 3 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Carbendazim Compositions on Weed Control in a Rice Cropping System.Compound A Visual Weed Control (%) - 19 DAA Benzyl Ester CarbendazimECHCO gae/ha gai/ha Obs Exp 8 0 65 — 16 0 90 — 32 0 95 — 0 125 0 — 0 2500 — 8 125 85 65 16 125 95 90 32 125 99 95 8 250 95 65 16 250 95 90 32250 95 95

TABLE 4 Synergistic Activity of Foliar-Applied Compound A Acid andDifenoconazole Compositions on Weed Control in a Rice Cropping System.Visual Weed Control Compound A (%) - 21 DAA Acid Difenoconazole DIGSAECHCG LEFCH gae/ha gai/ha Obs Exp Obs Exp Obs Exp 5.3 0 10 — 80 — 10 —10.6 0 20 — 90 — 20 — 21.2 0 20 — 95 — 45 — 0 200 0 — 0 — 0 — 5.3 200 1010 95 80 50 10 10.6 200 25 20 95 90 30 20 21.2 200 50 20 99 95 40 45

TABLE 5 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Difenoconazole Compositions on Weed Control in a Rice CroppingSystem. Compound A Visual Weed Control (%) - 21 DAA Benzyl EsterDifenoconazole LEFCH IPOHE gae/ha gai/ha Obs Exp Obs Exp 4.38 0 10 — 10— 8.75 0 20 — 10 — 17.5 0 55 — 20 — 0 200 0 — 0 — 4.38 200 30 10 10 108.75 200 45 20 30 10 17.5 200 50 55 40 20 Compound A Visual Weed Control(%) - 22 DAA Benzyl Ester Difenoconazole DIGSA gae/ha gai/ha Obs Exp 8 015 — 16 0 23 — 32 0 28 — 0 50 0 — 0 100 0 — 0 200 0 — 8 50 25 15 16 5028 23 32 50 45 28 8 100 40 15 16 100 53 23 32 100 55 28 8 200 55 15 16200 53 23 32 200 68 28 Compound A Visual Weed Control (%) - 21 DAABenzyl Ester Difenoconazole LEFCH gae/ha gai/ha Obs Exp 16 0 25 — 32 043 — 0 50 0 — 0 100 0 — 0 200 0 — 16 50 30 25 32 50 53 43 16 100 33 2532 100 60 43 16 200 48 25 32 200 70 43 Compound A Visual Weed Control(%) - 21 DAA Benzyl Ester Difenoconazole ECHCG gae/ha gai/ha Obs Exp 8 070 — 16 0 60 — 32 0 90 — 0 50 0 — 0 100 0 — 0 200 0 — 8 50 83 70 16 5090 60 32 50 93 90 8 100 80 70 16 100 88 60 32 100 95 90 8 200 88 70 16200 95 60 32 200 95 90 Compound A Visual Weed Control (%) - 21 DAABenzyl Ester Difenoconazole ECHOR gae/ha gai/ha Obs Exp 8 0 45 — 16 0 43— 32 0 70 — 0 50 0 — 0 100 0 — 0 200 0 — 8 50 58 45 16 50 63 43 32 50 9670 8 100 65 45 16 100 88 43 32 100 95 70 8 200 65 45 16 200 88 43 32 20093 70

TABLE 6 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Flutolanil Compositions on Weed Control in a Rice Cropping System.Compound A Visual Weed Control (%) - 19 DAA Benzyl Ester FlutolanilECHCO LEFCH gae/ha gai/ha Obs Exp Obs Exp 8 0 65 — 45 — 16 0 90 — 45 —32 0 95 — 50 — 0 280 0 — 0 — 0 560 0 — 0 — 8 280 85 65 60 45 16 280 9590 60 45 32 280 100 95 70 50 8 560 90 65 50 45 16 560 95 90 50 45 32 56099 95 55 50

TABLE 7 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Hexaconazole Compositions on Weed Control in a Rice Cropping System.Compound A Benzyl Ester Hexaconazole Visual Weed Control (%) - 21 DAAECHCG ECHCO LEFCH gae/ha gai/ha Obs Exp Obs Exp Obs Exp 8 0 45 — 50 — 25— 16 0 85 — 65 — 40 — 32 0 90 — 85 — 55 — 0 25 0 — 0 — 0 — 0 50 0 — 0 —0 — 0 100 0 — 0 — 0 — 8 25 80 45 75 50 40 25 16 25 90 85 90 65 50 40 3225 95 90 90 85 65 55 8 50 80 45 80 50 20 25 16 50 90 85 85 65 75 40 3250 90 90 95 85 60 55 8 100 85 45 90 50 45 25 16 100 90 85 90 65 55 40 32100 95 90 95 85 60 55 BRAPP IPOHE gae/ha gai/ha Obs Exp Obs Exp 8 0 55 —10 — 16 0 60 — 25 — 0 25 0 — 0 — 0 50 0 — 0 — 0 100 0 — 0 — 8 25 65 5530 10 16 25 85 60 35 25 8 50 50 55 20 10 16 50 80 60 60 25 8 100 65 5520 10 16 100 65 60 40 25 CYPIR gae/ha gai/ha Obs Exp 8 0 35 — 0 25 0 — 050 0 — 0 100 0 — 8 25 80 35 8 50 60 35 8 100 50 35

TABLE 8 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Isotianil Compositions on Weed Control in a Rice Cropping System.Compound A Benzyl Ester Isotianil Visual Weed Isotianil Control (%) - 20DAA BRAPP gae/ha gai/ha Obs Exp 8 0 60 — 16 0 85 — 32 0 90 — 0 200 0 — 8200 75 60 16 200 90 85 32 200 90 90 DIGSA gae/ha gai/ha Obs Exp 8 0 20 —16 0 30 — 32 0 40 — 0 100 0 — 0 200 0 — 8 100 30 20 16 100 55 30 32 10060 40 8 200 35 20 16 200 60 30 32 200 50 40 BRAPP DIGSA ECHCG ECHCOLEFCH gae/ha gai/ha Obs Exp Obs Exp Obs Exp Obs Exp Obs Exp 8 0 55 — 15— 45 — 50 — 25 — 16 0 60 — 25 — 85 — 65 — 40 — 0 380 0 — 0 — 0 — 0 — 0 —8 380 80 55 50 15 80 45 80 50 55 25 16 380 90 60 50 25 85 85 90 65 55 40

TABLE 9 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Kasugamycin Compositions on Weed Control in a Rice Cropping System.Compound A Benzyl Ester Kasugamycin Visual Weed Control (%) - 21 DAADIGSA ECHOR LEFCH IPOHE gae/ha gai/ha Obs Exp Obs Exp Obs Exp Obs Exp 80 20 — 20 — 40 — 0 — 16 0 40 — 60 — 40 — 30 — 32 0 50 — 85 — 65 — 55 — 017.5 0 — 0 — 0 — 0 — 0 35 0 — 0 — 0 — 0 — 0 70 0 — 0 — 0 — 0 — 8 17.5 3020 40 20 50 40 10 0 16 17.5 40 40 65 60 60 40 50 30 32 17.5 55 50 90 8575 65 65 55 8 35 25 20 60 20 50 40 25 0 16 35 40 40 80 60 70 40 50 30 3235 65 50 95 85 65 65 65 55 8 70 40 20 35 20 45 40 50 0 16 70 45 40 65 6055 40 45 30 32 70 60 50 95 85 70 65 70 55 CYPIR gae/ha gai/ha Obs Exp 80 50 — 16 0 70 — 0 17.5 0 — 0 35 0 — 0 70 0 — 8 17.5 85 50 16 17.5 10070 8 35 50 50 16 35 100 70 8 70 50 50 16 70 100 70 CYPES gae/ha gai/haObs Exp 8 0 70 — 0 17.5 0 — 0 35 0 — 0 70 0 — 8 17.5 95 70 8 35 70 70 870 85 70

TABLE 10 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Mancozeb Compositions on Weed Control in a Rice Cropping System.Visual Weed Compound A Control Benzyl Ester Mancozeb (%) - 21 DAA LEFCHgae/ha gai/ha Obs Exp 16 0 15 — 32 0 25 — 0 840 0 — 16 840 25 15 32 84045 25 IPOHE gae/ha gai/ha Obs Exp 8 0 10 — 16 0 50 — 32 0 60 — 0 1680 0— 8 1680 20 10 16 1680 70 50 32 1680 70 60

TABLE 11 Synergistic Activity of Foliar-Applied Compound A Acid andMyclobutanil Compositions on Weed Control in a Rice Cropping System.Compound A Visual Weed Control (%) - 21 DAA Acid Myclobutanil LEFCHIPOHE gae/ha gai/ha Obs Exp Obs Exp 5.3 0 10 — 10 — 10.6 0 20 — 15 —21.2 0 45 — 20 — 0 250 0 — 10 — 5.3 250 10 10 10 19 10.6 250 30 20 10 2421.2 250 70 45 65 28

TABLE 12 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Myclobutanil Compositions on Weed Control in a Rice Cropping System.Compound A Visual Weed Control Benzyl Ester Myclobutanil (%) - 21 DAALEFCH IPOHE gae/ha gai/ha Obs Exp Obs Exp 4.38 0 10 — 10 — 8.75 0 20 —10 — 17.5 0 55 — 20 — 0 250 0 — 10 — 4.38 250 30 10 10 19 8.75 250 60 2010 19 17.5 250 75 55 45 28 LEFCH gae/ha gai/ha Obs Exp 8 0 23 — 16 0 25— 32 0 43 — 0 200 0 — 8 200 30 23 16 200 50 25 32 200 65 43 ECHCG gae/hagai/ha Obs Exp 8 0 70 — 16 0 60 — 32 0 90 — 0 50 0 — 0 100 0 — 0 200 0 —8 50 88 70 16 50 90 60 32 50 97 90 8 100 90 70 16 100 93 60 32 100 95 908 200 90 70 16 200 93 60 32 200 95 90 ECHOR gae/ha gai/ha Obs Exp 8 0 45— 16 0 43 — 32 0 70 — 0 50 0 — 0 100 0 — 0 200 0 — 8 50 80 45 16 50 8543 32 50 95 70 8 100 90 45 16 100 93 43 32 100 97 70 8 200 85 45 16 20090 43 32 200 97 70

TABLE 13 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Probenazole Compositions on Weed Control in a Rice Cropping System.Visual Weed Control (%) - 19 Compound A DAA Benzyl Ester ProbenazoleECHCO gae/ha gai/ha Obs Exp 8 0 65 — 0 500 0 8 500 85 65

TABLE 14 Synergistic Activity of Foliar-Applied Compound A Acid andPropiconazole Compositions on Weed Control in a Rice Cropping System.Visual Weed Control (%) - 21 Compound A DAA Acid Propiconazole DIGSAgae/ha gai/ha Obs Exp 5.3 0 10 — 10.6 0 20 — 21.2 0 20 — 0 190 0 — 5.3190 0 10 10.6 190 40 20 21.2 190 40 20

TABLE 15 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Propiconazole Compositions on Weed Control in a Rice CroppingSystem. Visual Weed Control Compound A (%) - 20 DAA Benzyl EsterPropiconazole CYPES SCPJU gae/ha gai/ha Obs Exp Obs Exp 8 0 0 — 70 — 160 75 — 85 — 0 62.5 0 — 0 — 0 125 0 — 0 — 0 250 0 — 0 — 8 62.5 63 0 70 7016 62.5 85 75 95 85 8 125 80 0 95 70 16 125 80 75 100 85 8 250 73 0 9070 16 250 93 75 99 85

TABLE 16 Synergistic Activity of Foliar-Applied Compound A Acid andTebuconazole Compositions on Weed Control in a Rice Cropping System.Compound Visual Weed Control (%) - 21 DAA A Acid Tebuconazole DIGSAECHCG LEFCH IPOHE gae/ha gai/ha Obs Exp Obs Exp Obs Exp Obs Exp 5.3 0 10— 80 — 10 — 10 — 10.6 0 20 — 90 — 20 — 15 — 21.2 0 20 — 95 — 45 — 20 — 0250 0 — 0 — 0 — 0 — 5.3 250 25 10 95 80 10 10 15 10 10.6 250 40 20 95 9050 20 15 15 21.2 250 60 20 99 95 85 45 60 20

TABLE 17 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Tebuconazole Compositions on Weed Control in a Rice Cropping System.Visual Weed Control (%) - 21 Compound A DAA Benzyl Ester TebuconazoleLEFCH gae/ha gai/ha Obs Exp 4.38 0 10 — 8.75 0 20 — 17.5 0 55 — 0 250 0— 4.38 250 20 10 8.75 250 60 20 17.5 250 65 55 Visual Weed Control (%) -21 Compound A DAA Benzyl Ester Tebuconazole LEFCH gae/ha gai/ha Obs Exp8 0 23 — 16 0 25 — 32 0 43 — 0 62.5 5 — 0 125 10 — 0 250 8 — 8 62.5 5526 16 62.5 53 29 32 62.5 75 45 8 125 50 30 16 125 58 33 32 125 70 48 8250 43 28 16 250 60 31 32 250 80 47 Visual Weed Control (%) - 22Compound A DAA Benzyl Ester Tebuconazole BRAPP gae/ha gai/ha Obs Exp 8 065 — 0 62.5 0 — 0 125 0 — 0 250 0 — 8 62.5 78 65 8 125 63 65 8 250 85 65Visual Weed Control (%) - 22 Compound A DAA Benzyl Ester TebuconazoleCYPIR gae/ha gai/ha Obs Exp 8 0 75 — 16 0 73 — 32 0 60 — 0 125 0 — 0 2500 — 8 125 68 75 16 125 90 73 32 125 100 60 8 250 100 75 16 250 100 73 32250 100 60 Visual Weed Control (%) - 22 Compound A DAA Benzyl EsterTebuconazole IPOHE gae/ha gai/ha Obs Exp 8 0 15 — 16 0 33 — 0 62.5 0 — 862.5 30 15 16 62.5 53 33 Visual Weed Control (%) - 21 Compound A DAABenzyl Ester Tebuconazole ECHCG gae/ha gai/ha Obs Exp 8 0 70 — 16 0 60 —32 0 90 — 0 62.5 0 — 0 125 5 — 0 250 8 — 8 62.5 90 70 16 62.5 95 60 3262.5 95 90 8 125 88 72 16 125 90 62 32 125 95 91 8 250 93 72 16 250 9063 32 250 97 91 Visual Weed Control (%) - 21 Compound A DAA Benzyl EsterTebuconazole ECHOR gae/ha gai/ha Obs Exp 8 0 45 — 16 0 43 — 32 0 70 — 062.5 0 — 0 125 5 — 0 250 8 — 8 62.5 90 45 16 62.5 90 43 32 62.5 97 70 8125 93 48 16 125 95 45 32 125 95 72 8 250 88 49 16 250 95 47 32 250 9572 Visual Weed Control (%) - 22 Compound A DAA Benzyl Ester TebuconazoleDIGSA gae/ha gai/ha Obs Exp 8 0 15 — 16 0 23 — 32 0 28 — 0 62.5 0 — 0125 0 — 0 250 0 — 8 62.5 38 15 16 62.5 53 23 32 62.5 60 28 8 125 43 1516 125 40 23 32 125 58 28 8 250 45 15 16 250 45 23 32 250 63 28

TABLE 18 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Thifluzamide Compositions on Weed Control in a Rice Cropping System.Visual Weed Control Compound A (%) - 20 DAA Benzyl Ester ThifluzamideBRAPP DIGSA gae/ha gai/ha Obs Exp Obs Exp 8 0 60 — 20 — 16 0 85 — 30 —32 0 90 — 40 — 0 75 0 — 0 — 0 150 0 — 0 — 0 300 0 — 0 — 8 75 80 60 30 2016 75 75 85 45 30 32 75 95 90 45 40 8 150 80 60 50 20 16 150 95 85 40 3032 150 95 90 50 40 8 300 80 60 35 20 16 300 85 85 30 30 32 300 95 90 3540

TABLE19 Synergistic Activity of Foliar-Applied Compound A Acid andTricyclazole Compositions on Weed Control in a Rice Cropping System.Visual Weed Control (%) - 21 Compound A DAA Acid Tricyclazole IPOHEgae/ha gai/ha Obs Exp 5.3 0 10 — 10.6 0 15 — 21.2 0 20 — 0 200 0 — 5.3200 30 10 10.6 200 25 15 21.2 200 60 20

TABLE 20 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Tricyclazole Compositions on Weed Control in a Rice Cropping System.Visual Weed Control (%) - 21 Compound A DAA Benzyl Ester TricyclazoleIPOHE gae/ha gai/ha Obs Exp 4.38 0 10 — 8.75 0 10 — 17.5 0 20 — 0 200 0— 4.38 200 15 10 8.75 200 15 10 17.5 200 40 20 Visual Weed Control (%) -21 Compound A DAA Benzyl Ester Tricyclazole ECHCG gae/ha gai/ha Obs Exp8 0 70 — 16 0 60 — 32 0 90 — 0 50 0 — 0 100 0 — 0 200 0 — 8 50 75 70 1650 80 60 32 50 95 90 8 100 65 70 16 100 78 60 32 100 93 90 8 200 85 7016 200 90 60 32 200 95 90 Visual Weed Control (%) - 21 Compound A DAABenzyl Ester Tricyclazole ECHOR gae/ha gai/ha Obs Exp 8 0 45 — 16 0 43 —32 0 70 — 0 50 0 — 0 100 0 — 0 200 0 — 8 50 58 45 16 50 68 43 32 50 9070 8 100 48 45 16 100 55 43 32 100 93 70 8 200 58 45 16 200 78 43 32 20090 70 Visual Weed Control (%) - 22 Compound A DAA Benzyl EsterTricyclazole IPOHE gae/ha gai/ha Obs Exp 8 0 15 — 16 0 33 — 0 50 0 — 0100 0 — 0 200 10 — 8 50 28 15 16 50 55 33 8 100 15 15 16 100 55 33 8 20038 24 16 200 45 39

TABLE 21 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Trifloxystrobin Compositions on Weed Control in a Rice CroppingSystem. Visual Weed Compound A Control Benzyl Ester Trifloxystrobin(%) - 21 DAA CYPIR gae/ha gai/ha Obs Exp 8 0 50 — 16 0 70 — 32 0 100 — 0140 0 — 8 140 70 50 16 140 95 70 32 140 100 100 Visual Weed Compound AControl Benzyl Ester Trifloxystrobin (%) - 20 DAA DIGSA gae/ha gai/haObs Exp 8 0 15 — 0 75 0 — 0 150 0 — 0 300 0 — 8 75 30 15 8 150 10 15 8300 30 15 Visual Weed Compound A Control Benzyl Ester Trifloxystrobin(%) - 20 DAA CYPES gae/ha gai/ha Obs Exp 16 0 40 — 0 75 0 — 0 150 0 — 1675 70 40 16 150 60 40

TABLE 22 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand a compound of formula (II) Compositions on Weed Control in a RiceCropping System. Visual Weed Compound A Compound of Control Benzyl EsterFormula (II) (%) - 21 DAA BRAPP gae/ha gai/ha Obs Exp 8 0 70 — 0 37.5 0— 0 75 0 — 0 150 0 — 8 37.5 80 70 8 75 90 70 8 150 90 70 ECHCG gae/hagai/ha Obs Exp 16 0 80 — 32 0 95 — 0 150 0 — 16 150 95 80 32 150 99 95LEFCH gae/ha gai/ha Obs Exp 32 0 25 — 0 37.5 0 — 0 75 0 — 0 150 0 — 3237.5 40 25 32 75 50 25 32 150 30 25 CYPIR gae/ha gai/ha Obs Exp 8 0 50 037.5 0 0 75 0 8 37.5 70 50 8 75 100 50BRAPP Brachiaria platyphylla (Groseb.) Nash, broadleaf signalgrass.CYPES Cyperus esculentus L., nutsedge, yellowCYPIR Cyperus iria L., flatsedge, riceDIGSA Digitaria sanguinalis (L.) Scop.; crabgrass, largeECHCG Echinochloa crus-galli (L.) Beauv.; barnyardgrassECHCO Echinochloa colona (L.) Link; junglericeIPOHE Ipomoea hederacea Jacq.; morningglory, ivyleafLEFCH Leptochloa chinensis (L.) Nees; sprangletop, ChineseSCPJU Schoenoplectus juncoides Roxb., bulrush, Japanesegae/ha=grams acid equivalent per hectaregai/ha=grams active ingredient per hectareObs=observed valueExp=expected value as calculated by Colby's equationDAA=days after application

Example II Evaluation of 1n-Water Applied Herbicidal Mixtures for WeedControl in Transplanted Paddy Rice

Weed seeds or nutlets of the desired test plant species were planted inpuddled soil (mud) prepared by mixing a shredded, non-sterilized mineralsoil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with apH of about 7.6 and an organic matter content of about 2.9 percent) andwater at a 1:1 volumetric ratio. The prepared mud was dispensed in 365mL aliquots into 16-ounce (oz.) non-perforated plastic pots with asurface area of 86.59 square centimeters leaving a headspace of 3centimeters in each pot. Rice seeds were planted in Sun Gro MetroMix®306 planting mixture, which typically has a pH of 6.0 to 6.8 and anorganic matter content of about 30 percent, in plastic plug trays.Seedlings at the second or third leaf stage of growth were transplantedinto 860 mL of mud contained in 32-oz. non-perforated plastic pots witha surface area of 86.59 cm² 4 days prior to herbicide application. Thepaddy was created by filling the headspace of the pots with 2.5 to 3 cmof water. When required to ensure good germination and healthy plants, afungicide treatment and/or other chemical or physical treatment wasapplied. The plants were grown for 4-22 days in a greenhouse with anapproximate 14 h photoperiod which was maintained at about 29° C. duringthe day and about 26° C. during the night. Nutrients were added asOsmocote® (17:6:10, N:P:K+minor nutrients) at 2 g per cup. Water wasadded on a regular basis to maintain the paddy flood, and supplementallighting was provided with overhead metal halide 1000-Watt lamps asnecessary. The plants were employed for testing when they reached thefirst through fourth true leaf stage.

Treatments consisted of the acid or esters of4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylicacid (compound A) each formulated as an SC (suspension concentrate) andvarious fungicidal components alone and in combination. Forms ofcompound A were applied on an acid equivalent basis.

Forms of compound A (compound of formula I) tested include:

Other fungicidal components were applied on an active ingredient basisand consisted of flutolanil (technical grade material), probenazole(technical grade material), and tricyclazole formulated as Beam®.

Treatment requirements for each compound or fungicidal component werecalculated based upon the rates being tested, the concentration ofactive ingredient or acid equivalent in the formulation, an applicationvolume of 2 mL per component per pot, and an application area of 86.59cm² per pot.

For formulated compounds, a measured amount was placed in an individual100 or 200 mL glass vial and was dissolved in a volume of 1.25% (v/v)Agri-Dex® crop oil concentrate to obtain application solutions. If thetest compound did not dissolve readily, the mixture was warmed and/orsonicated.

For technical grade compounds, a weighed amount can be placed in anindividual 100 to 200 mL glass vial and dissolved in a volume of acetoneto obtain concentrated stock solutions. If the test compound does notdissolve readily, the mixture can be warmed and/or sonicated. Theconcentrated stock solutions obtained can be diluted with an equivalentvolume of an aqueous mixture containing 2.5% (v/v) crop oil concentrateso that the final application solutions contain 1.25% (v/v) crop oilconcentrate.

Applications were made by injecting with a pipetter appropriate amountsof the application solutions, individually and sequentially, into theaqueous layer of the paddy. Control plants were treated in the samemanner with the solvent blank. Applications were made so that alltreated plant material received the same concentrations of acetone andcrop oil concentrate.

The treated plants and control plants were placed in a greenhouse asdescribed above and water was added as needed to maintain a paddy flood.After approximately 3 weeks the condition of the test plants as comparedwith that of the untreated plants was determined visually and scored ona scale of 0 to 100 percent where 0 corresponds to no injury or growthinhibition and 100 corresponds to complete kill.

Colby's equation was used to determine the herbicidal effects expectedfrom the mixtures (Colby, S.R. 1967. Calculation of the synergistic andantagonistic response of herbicide combinations. Weeds 15:20-22.).

The following equation was used to calculate the expected activity ofmixtures containing two active ingredients, A and B:Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration asused in the mixture.

B=observed efficacy of active ingredient B at the same concentration asused in the mixture.

Some of the compounds tested, application rates employed, plant speciestested, and results are given in Tables 23-26.

TABLE 23 Synergistic Activity of In-Water Applied Compound A BenzylEster and a Compound of Formula (II) Compositions on Weed Control in aTransplanted Rice Cropping System. Visual Weed Compound A Control BenzylEster Flutolanil (%) - 21 DAA ECHOR gae/ha gai/ha Obs Exp 8 0 15 — 16 020 — 0 140 0 — 0 560 0 — 8 140 45 15 16 140 75 20 8 560 30 15 16 560 5020 LEFCH gae/ha gai/ha Obs Exp 8 0 0 — 16 0 0 — 0 140 0 — 8 140 20 0 16140 20 0

TABLE 24 Synergistic Activity of In-Water Applied Compound A BenzylEster and Probenazole Compositions on Weed Control in a TransplantedRice Cropping System. Visual Weed Control (%) - 21 Compound A DAA BenzylEster Probenazole CYPRO gae/ha gai/ha Obs Exp 8 0 40 — 0 1000 0 — 0 20000 — 0 4000 0 — 8 1000 95 40 8 2000 80 40 8 4000 75 40

TABLE 25 Synergistic Activity of In-Water Applied Compound A Acid andTricyclazole Compositions on Weed Control in a Transplanted RiceCropping System. Visual Weed Control (%) - 22 Compound A DAA AcidTricyclazole CYPRO gae/ha gai/ha Obs Exp 10.6 0 0 — 21.2 0 25 — 42.4 095 — 0 200 0 — 10.6 200 80 0 21.2 200 70 25 42.4 200 90 95

TABLE 26 Synergistic Activity of In-Water Applied Compound A BenzylEster and Tricyclazole Compositions on Weed Control in a TransplantedRice Cropping System. Visual Weed Control Compound A (%) - 19 DAA BenzylEster Tricyclazole CYPRO gae/ha gai/ha Obs Exp 8 0 20 — 16 0 88 — 32 087 — 0 375 0 — 0 750 0 — 8 375 10 20 16 375 83 88 32 375 98 87 8 750 5020 16 750 80 88 32 750 88 87 Visual Weed Control Compound A (%) - 22 DAABenzyl Ester Tricyclazole FIMMI gae/ha gai/ha Obs Exp 4.38 0 50 — 8.75 080 — 17.5 0 100 — 0 200 0 — 4.38 200 100 50 8.75 200 100 80 17.5 200 100100 Visual Weed Control Compound A (%) - 19 DAA Benzyl EsterTricyclazole LEFCH gae/ha gai/ha Obs Exp 8 0 3 — 16 0 8 — 0 187.5 0 — 0750 0 — 8 187.5 3 3 16 187.5 20 8 8 750 17 3 16 750 13 8CYPRO Cyperus rotundus L.; nutsedge, purpleECHCO Echinochloa colona (L.) Link; junglericeFIMMI Fimbristylis miliacea (L.) Vahl; globe fringerushLEFCH Leptochloa chinensis (L.) Nees; sprangletop, Chinesegae/ha=grams acid equivalent per hectaregai/ha=grams active ingredient per hectareObs=observed valueExp=expected value as calculated by Colby's equationDAA=days after application

What is claimed is:
 1. A herbicidal composition comprising aherbicidally effective amount of (a) a compound of the formula (I):

or an alkyl or benzyl ester, or an agriculturally acceptable salt offormula (I) and (b) a compound selected from the group consisting of:azoxystrobin, carbendazim, difenoconazole, flutolanil, hexaconazole,isotianil, kasugamycin, mancozeb, myclobutanil, probenazole,propiconazole, tebuconazole, thifluzamide, tricyclazole,trifloxystrobin, and a compound of formula (II):

wherein (a) and (b) are present in the composition in a ratio such thatthe composition exhibits herbicidal synergy.
 2. The composition of claim1, wherein (a) is a benzyl ester of the compound of formula (I).
 3. Thecomposition of claim 1, wherein (a) is a C₁₋₄ alkyl ester of thecompound of formula (I).
 4. The composition of claim 1, wherein (a) isthe carboxylic acid of the compound of formula (I).
 5. The compositionof claim 1, further comprising at least one compound selected from thegroup consisting of: herbicide safeners, carriers and adjuvants.
 6. Thecomposition of claim 1, wherein the weight ratio of compound of formula(I) or agriculturally acceptable salt or ester thereof to a compound offormula (II) is from about 1:375 to about 150:1.
 7. A method ofcontrolling undesirable vegetation, comprising the steps of: contactinga plant, wherein the plant is undesirable vegetation, the area adjacentto the plant, soil or water, wherein the soil or the water allows forthe growth of the undesirable vegetation, with a herbicidally effectiveamount of a combination comprising (a) a compound of the formula (I):

or an alkyl or benzyl ester, or an agriculturally acceptable salt offormula (I) and (b) a compound selected from the group consisting of:azoxystrobin, carbendazim, difenoconazole, flutolanil, hexaconazole,isotianil, kasugamycin, mancozeb, myclobutanil, probenazole,propiconazole, tebuconazole, thifluzamide, tricyclazole,trifloxystrobin, and a compound of formula (II):

wherein (a) and (b) are present in the combination in a ratio such thatthe combination exhibits herbicidal synergy; wherein the undesirablevegetation is controlled in direct-seeded, water-seeded and transplantedrice, cereals, wheat, barley, oats, rye, sorghum, maize and canola. 8.The method of claim 7, wherein the undesirable vegetation is immature.9. The method of claim 7, wherein the (a) and (b) are applied to water.10. The method of claim 9, wherein the water is part of a flooded ricepaddy.
 11. The method of claim 7, wherein the (a) and (b) are appliedpre-emergently and/or post emergently to the undesirable vegetation in acrop.
 12. The method of claim 7, wherein the (a) and (b) are appliedpost-emergently to the undesirable vegetation in a crop.
 13. The methodof claim 7, wherein the undesirable vegetation is controlled inglyphosate-, 5-enolpyruvylshikimate-3-phosphate synthase inhibitor-,glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-,pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-,aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetylCoA carboxylase inhibitor-, imidazolinone-, sulfonylurea-,pyrimidinylthiobenzoate-, triazolopyrimidine-,sulfonylaminocarbonyltriazolinone-, acetolactate synthase oracetohydroxy acid synthase inhibitor-, 4-hydroxyphenyl-pyruvatedioxygenase inhibitor-, phytoene desaturase inhibitor-, carotenoidbiosynthesis inhibitor-, protoporphyrinogen oxidase inhibitor-,cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubuleinhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipidbiosynthesis inhibitor-, photosystem I inhibitor-, photosystem IIinhibitor-, triazine-, or bromoxynil-tolerant crops.
 14. The method ofclaim 13, wherein the tolerant crop possesses multiple or stacked traitsconferring tolerance to multiple herbicides.
 15. The method of claim 7,wherein the undesirable vegetation comprises a herbicide resistant ortolerant plant.
 16. The method of claim 15, wherein the resistant ortolerant plant is resistant or tolerant to multiple herbicides.
 17. Themethod of claim 15, wherein the resistant or tolerant plant is resistantor tolerant to acetolactate synthase or acetohydroxy acid synthaseinhibitors, photosystem II inhibitors, acetyl CoA carboxylaseinhibitors, synthetic auxins, auxin transport inhibitors, photosystem Iinhibitors, 5-enolpyruvylshikimate-3-phosphate synthase inhibitors,microtubule assembly inhibitors, fatty acid and lipid synthesisinhibitors, protoporphyrinogen oxidase inhibitors, carotenoidbiosynthesis inhibitors, very long chain fatty acid inhibitors, phytoenedesaturase inhibitors, glutamine synthetase inhibitors,4-hydroxyphenyl-pyruvate-dioxygenase inhibitors, mitosis inhibitors,cellulose biosynthesis inhibitors, herbicides with multiplemodes-of-action, quinclorac, arylaminopropionic acids, difenzoquat,endothall, or organoarsenicals.
 18. The method of claim 16, wherein theresistant or tolerant plant is resistant or tolerant to acetolactatesynthase or acetohydroxy acid synthase inhibitors, photosystem IIinhibitors, acetyl CoA carboxylase inhibitors, synthetic auxins, auxintransport inhibitors, photosystem I inhibitors,5-enolpyruvylshikimate-3-phosphate synthase inhibitors, microtubuleassembly inhibitors, fatty acid and lipid synthesis inhibitors,protoporphyrinogen oxidase inhibitors, carotenoid biosynthesisinhibitors, very long chain fatty acid inhibitors, phytoene desaturaseinhibitors, glutamine synthetase inhibitors,4-hydroxyphenyl-pyruvate-dioxygenase inhibitors, mitosis inhibitors,cellulose biosynthesis inhibitors, herbicides with multiplemodes-of-action, quinclorac, arylaminopropionic acids, difenzoquat,endothall, or organoarsenicals.